Indolines-derivatives

Electric Literature of 18711-15-4,Some common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A reaction flask with high vacuum valve was charged with 2-amino-N?-arylbenzohydrazides (1.0 mmol), 4-halogenated isatins (1.0 mmol), CuI (10 mg, 0.05 mmol), and Cs2CO3 (650 mg, 2.0 mmol). After being degassed by three freeze-thaw pump cycles, THF (10.0 mL) was injected into the mixture. And then, the reaction mixture was stirred at reflux for 10-16 h before reaching completion, which was monitored by TLC. The solvent was recovered by distillation under reduced pressure, and the residue was purified by chromatography over silica gel to give 3 using ethyl acetate and petroleum ether (1:2) as an eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,6-Dichloroisatin, its application will become more common.

Application of 550-44-7, The chemical industry reduces the impact on the environment during synthesis 550-44-7, name is 2-Methylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H9NO2

e) 2-(1-Acetyl-1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione 1-Acetyl-1,2-dihydroindol-3-one of Example 1d (131.3 g, 0.75 mol) and 5,5-dimethyl-cyclohexane-1,3-dione (105 g, 0.75 mol) were added to a mixture of acetic acid (700 mL) and triethylamine (105 mL, 0.75 mol) at room temperature under stirring. The reaction mixture was refluxed for 6 h. About 1/3 volume of solvents was removed in vacuum, and the mixture was cooled and diluted with water (50 mL). The precipitate was filtered off, washed with ethanol-water, 1:1 and dried to afford 169.4 g (76%) of colorless crystals; m.p. 225-227 C.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Application of 17564-64-6, A common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Conditions A: aqueous 37% hydrochloric acid (0.17 mL, 2 mmol) was added to a solution of 1 (258 mg, 1.0 mmol) in 8 mL of degassed ethanol. The mixture was heated at 95 C under Argon atmosphere until the selenocarbonate 1 disappeared (2,5-3 h). After cooling to room temperature sodium bicarbonate (0.34 g, 4 mmol) and alkylhalide (1.5 mmol, see Table 3) were added and the resulting mixture was stirred until the end of the reaction (TLC analysis). After the addition of water (10 mL) the mixture was extracted three times with 10 mL of EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified on a silica gel column with a mixture of petroleum ether and ethyl ether as eluant to give the corresponding selenide 5. Conditions B: trifluoroacetic acid (0.15 mL, 2 mmol) was added to a solution of 1 (258 mg, 1.0 mmol) in 8 mL of degassed DMF. The mixture was heated at 95 C under Argon atmosphere until the selenocarbonate 1 disappeared (2,5-3 h). After cooling to room temperature sodium acetate (0.33 g, 4 mmol) and alkyl or aryl halide (1.5 mmol, see Table 3) were added and the resulting mixture was stirred until the end of the reaction (TLC analysis). After the addition of water (10 mL) the mixture was extracted three times with 10 mL of EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The corresponding selenide 5 was isolated after column chromatographyon SiO2 utilizing a mixture of diethyl ether and petroleum ether as eluant. Characterisation data for selenides 5b-5c [26], 5d, [27] 5e, [28] 5f [29], 5g [30], 5h [31], and 5i [32] matched the ones previously reported in literature for these compounds.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

tert-Butyl 3-bromo-4-oxo-piperidine-1-carboxylate (2 g, 7.2 mmol) was suspended in THF (2 mL) and cooled in an ice bath before addition of dimethylamine (16 mL of 2 M, 32 mmol). Upon complete addition, the ice bath was removed and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in THF (28 mL) under N2. The solution was cooled to -78 C and LiHMDS (10 mL of 1 M, 10 mmol) was added dropwise. After 40 minutes, 2- (chloromethyl)isoindoline-1,3-dione (2.32 g, 11.8 mmol) was added in portions over 5 minutes. The solution was stirred for 1 hour then left to warm up to 0 C before being quenched by addition of saturated aqueous NH4Cl solution. The mixture was partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 0-10% MeOH/DCM gradient elution) to give tert-butyl 3-(dimethylamino)-5-[(1,3-dioxoisoindolin-2- yl)methyl]-4-oxo-piperidine-1-carboxylate (1.58 g, 50%); MS m/z: 402 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)isoindoline-1,3-dione, its application will become more common.

Related Products of 104618-32-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 104618-32-8 as follows.

A solution of N-(4-oxocyclohexyl)phthalimide (14, 5.00 g, 21 mmol, 1 eq.) and 4-methoxyphenylhydrazine hydrochloride (3.59 g, 21 mmol, 1 eq.) in dry ethanol (100 mL) was heated at reflux for 2.5 h. After cooling down to room temperature, the precipitate was filtrated off and washed with ethanol 96% (3 * 10 mL). The solid was dried under reduced pressure and freeze-dried overnight. Rf = 0.66 (cyclohexane/ethyl acetate/dimethylethylamine 5:5:0.2). Colorless solid, mp 222-223 C, yield 6.88 g (97%). Purity (HPLC): 84.1% (tR = 22.2 min). C21H18N2O3 (346.4 g/mol). Exact mass (APCI): m/z = 347.1389 (calcd. 347.1390 for C21H19N2O3 [M + H+]). 1H NMR (400 MHz, DMSO-D6): delta (ppm) = 2.03-2.11 (m, 1H, 2-H), 2.67 (tt, J = 12.3/6.4 Hz, 1H, 2-H), 2.80-2.98 (m, 3H, 1-CH2, 4-H), 3.20-3.28 (m, 1H, 4-H), 3.71 (s, 3H, OCH3), 4.43-4.52 (m, 1H, 3-H), 6.65 (dd, J = 8.7/2.4 Hz, 1H, 7-H), 6.82 (d, J = 2.4 Hz, 1H, 5-H), 7.15 (d, J = 8.7 Hz, 1H, 8-H), 7.84-7.91 (m, 4H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 10.61 (s, 1H, NH). 13C NMR (101 MHz, DMSO-D6): delta (ppm) = 22.6 (1C, C-1), 24.7 (1C, C-4), 26.5 (1C, C-2), 47.8 (1C, C-3), 55.3 (1C, OCH3), 99.7 (1C, C-5), 106.3 (1C, C-4a), 109.9 (1C, C-7), 111.2 (1C, C-8), 123.0 (2C, C-4phth, C-7phth), 127.2 (1C, C-4b), 131.3 (1C, C-8a), 131.5 (2C, C-3aphth, C-7aphth), 134.2 (1C, C-9a), 134.4 (2C, C-5phth, C-6phth), 153.0 (1C, C-6), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3425 (w, N-H), 3379 (w, C-H, arom), 2924 (w, C-H, aliph), 1697 (s, C=O), 1597 (w, C-C, arom).

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference of 611-09-6, A common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of isatin derivatives (1a-1d, 1 mmol) oracenaphthoquinone (5, 1 mmol), methylene nitriles (2a,2b, 1 mmol), 1,3-dicarbonyl (3, 1 mmol), and 5 mg IG in3 cm3 H2O was stirred at 60 C for the mentioned timeshown in tables. Rapid conversion of reagents can beclearly confirmed by reaction color change. The progress ofthe reaction was monitored by TLC using EtOAc/n-hexane(1:3) as an eluent. Upon completion, the reaction mixturewas allowed to cool to room temperature and the precipitatewas obtained from the reaction mixture by filtration.The product 4a was dissolved in DMSO and the catalystwas separated by simple filtration. Pure products wereafforded by evaporation of the solvent under reduced pressure.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 18711-15-4, name is 4,6-Dichloroisatin, A new synthetic method of this compound is introduced below., Product Details of 18711-15-4

Example 15,7-Dichloro-4-(5-chloro-2-methoxyphenyl)-3-hydroxy-2(1H)-quinolinone and its regioisomer 5,7-dichloro-3-(5-chloro-2-methoxyphenyl)-4-hydroxy-2(1H)-quinolinone A mixture of 4,6-dichloro-1 H-indol-2,3-dione (6.48 g, 0.03 mol), 5-chloro-2-methoxy-[N-(4-methylphenyl)hydrazonomethyl]phenyl (10.65 g, 0.0315 mol, 1.05 eq.) and NaOMe (90 mL of 1.0 M solution in methanol) in methanol (150 mL) was heated at reflux temperature for 3 hours. The reaction mixture was cooled and the solid was collected by filtration and washed with methanol (3 x 10 mL). The solid was suspended in 0.5 N HCl solution (500 mL), stirred for 20 minutes then filtered, washed with water (3 x 50 mL) and dried to yield 2.76 g of the desired isomer 5,7-dichloro-4-(5-chloro-2-methoxyphenyl)-3-hydroxy-2(1H)-quinolinone.1H NMR (300 MHz, DMSO-d6) delta: 7.39 (dd, 1H, J = 2.7, 8.8 Hz), 7.36, (1H, d, J = 2.2 Hz), 7.23 (1H, d, J = 2.2 Hz), 7.15 (1H, d, J = 2.2 Hz), 7.02 (1H, d, J = 8.9 Hz), 3.64 (3H, s), 12.53 (1H, bs), 9.79 (1H, bs).13C NMR (75 MHz, DMSO-d6) delta: 157.2, 156.0, 145.4, 135.4, 130.2, 130.0, 130.0, 128.8, 126.3, 124.5, 123.6, 118.5, 116.6, 114.4, 112.2, 55.7. UV(abs. ethanol at 5.2 x 10-4 g/100 mL) lambdamax: 232 (1107), 336 (299) , 288 (292), 322 (289) and 310 (221); MS (DCI): 370 (MH+); IR (KBr, cm-1): 3500-2400, 1665, 1300-1200 and 1020. [] Anal. calcd. for C16H10Cl3NO3 C, 51.85;H, 2.72;N, 3.78.FoundC, 51.89;H, 2.81;N, 3.74. The filtrate from the above reaction mixture was added to 0.5 N HCl solution (1500 mL) with stirring. The product which precipitated from the acidified mixture was collected by filtration and dried to yield 8.11 g of a mixture (6:1) of the regioisomer 5,7-dichloro-3-(5-chloro-2-methoxyphenyl)-4-hydroxy-2(1H)-quinolinone and some of the desired product. A sample of the purified regioisomer had the following characteristics:1H NMR (300 MHz, DMSO-d6) delta: 11.70 (1H, s), 10.08 (1H, s), 7.37 (1H, dd, J = 2.7, 8.9 Hz), 7.29 (2H, d, J = 1.6 Hz), 7.13 (1H, d, J = 2.6 Hz), 7.05 (1H, d, J = 8.9 Hz), 3.68 (3H, s);13C NMR (75 MHz, DMSO-d6) delta: 156.9, 141.2, 134.3, 132.2, 131.6, 128.9, 124.1, 123.6, 113.8, 113.1, 55.7; UV(abs. ethanol at 4.8 x 10-4 g/100 mL) lambdamax: 234 (1480), 296 (373) and 326 (300) nm; MS (DCI): 370 (MH+); IR (KBr, cm-1): 3500-2500, 1660 and 1250. [] Anal. calcd. for C16H10Cl3NO3 C, 51.85;H, 2.72;N, 3.78.FoundC, 52.01;H, 2.76;N, 3.80.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5332-26-3, Product Details of 5332-26-3

To a stirred solution of 26 (50.0 g, 0.142 mol) in THF (500 mL) was added NaHMDS (2 M in THF, 106.2 mL, 0.213 mol) at 0 C and the resultant mixture was stirred for about 30 min. Then 2-(bromomethyl)isoindoline-1,3-dione (17; 41.0 g, 0.171 mol) was added at 0 C and the resultant reaction mixture was stirred for about 30 min. The reaction mixture was quenched with H2O (500 mL) at 0 C and extracted with EtOAc (2 × 500 mL). The combined organic layers were washed with H2O and brine, and concentrated to get the crude compound of 27, which was purified by column chromatography using PE/EtOAc (8.5:1.5) as eluent to afford the desired compound 27 as a colorless syrup; yield: 51 g (70%). 1H NMR (400 MHz, CDCl3): delta= 7.87-7.84 (m, 2 H), 7.78-7.75 (m, 2 H),7.42-7.33 (m, 5 H), 5.80 (br s, 1 H), 5.25-5.18 (m, 2 H), 4.32 (s, 2 H),4.18 (q, J= 7.2 Hz, 2 H), 3.74-3.61 (m, 2 H), 1.45 (s, 9 H), 1.19 (t, J= 6.8Hz, 3 H). 13C NMR (100 MHz, CDCl3): delta= 168.6, 168.5, 168.4, 155.5, 135.4,134.4, 131.6, 128.4, 128.3, 128.2, 123.7, 123.6, 79.3, 67.6, 62.1, 57.6,40.9, 38.7, 28.3, 13.7.LCMS: m/z= 511 [M + 1]. HRMS: m/z[M]+calcd for C27H31N2O8+: 511.2075; found: 511.2068.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 3676-85-5

Example 250Preparation of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)-amide To a stirred solution of thionyl chloride (2 mL), rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (110 mg, 0.24 mmol) was added and the mixture was stirred at rt for 2 hrs. The excess thionyl chloride was removed and the residue was dissolved in methylene chloride (5 mL) and 5-amino-isoindole-1,3-dione (Aldrich, 0.30 mmol) was added followed by the addition of triethylamine (0.2 mL). The mixture was stirred overnight. The solvent was removed and the residue was purified on an ISCO machine (24 g column, eluent, 40-80% EtOAc/hexanes) to give a pale yellow solid. 10 mg.MS (ES+) m/z Calcd: [(M+H)+]: 611, found: 611

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.