Tag: M.W=100-200

Some common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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. 603-62-3

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) 7.69 (brs, 1H, NHH), 7.74 (t, J = 8 Hz, 1H, Ar), 7.92 (dd, J = 1, 8 Hz, 1H, Ar), 8.13 (dd, J = 1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 603-62-3, its application will become more common.

Reference:
Patent; CELGENE CORPORATION; CHAMBERLAIN, Philip; CATHERS, Brian, E.; LOPEZ-GIRAONA, Antonia; (672 pag.)WO2015/200795; (2015); A1;,
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480-91-1, 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 480-91-1 as follows.

General procedure: A solution of POCl3 or POBr3 (30 mmol) in anhydrous DCM (7 mL) was added dropwise to DMF or DMA (30 mmol) in anhydrous DCM (15 mL) at 0 C. The mixture was stirred for 30 min at room temperature. Then, a solution of 1H-isoindolinone 1 (2 g, 15 mmol) in anhydrous DCM (75 mL) was added to the mixture, at 0 C. Subsequently, the reaction mixture was heated at reflux for 5 h, and then after cooling, the solvent was removed at reduced pressure. Ice-water was added, and the mixture was neutralized with NaOH 5 M. The precipitate was filtered out, washed with water and dried. The residue was recrystallized from MeOH/H2O (1:1) to give the following compounds.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 480-91-1, and friends who are interested can also refer to it.

Reference:
Article; Diana, Patrizia; Martorana, Annamaria; Barraja, Paola; Montalbano, Alessandra; Carbone, Anna; Cirrincione, Girolamo; Tetrahedron; vol. 67; 11; (2011); p. 2072 – 2080;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 317-20-4 name is 7-Fluoroisatin, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 317-20-4

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroisatin, and friends who are interested can also refer to it.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
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317-20-4, Name is 7-Fluoroisatin, 317-20-4, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step 1: Preparation of 7-fluoro-1-methyl-1H-indole-2,3-dione 7-Fluoro-1H-indole-2,3-dione (prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325, 1.0 g, 6.05 mmol), iodomethane (1.13 ml, 18.2 mmol) and potassium carbonate (1.65 g, 12.1 mmol) in DMF (15 ml) are stirred at room temperature for 24 hours. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4), and evaporated to give the title compound as an orange solid. HPLC r.t. 3.79 min; MS for C9H1FNO2 m/z 180.0(M+H)+.

Statistics shows that 7-Fluoroisatin is playing an increasingly important role. we look forward to future research findings about 317-20-4.

Reference:
Patent; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
Indoline – Wikipedia,
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14192-26-8,Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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.

In the four 3000mL round-bottomed flask, fitted with mechanical stirring, reflux condenser, thermometer, nitrogen was added to a 1500mL round bottom flask of toluene, 240g6- methoxycarbonyl-2-oxo-indoline, chlorine 272g acetic anhydride, open stirring, temperature was raised to 80 ~ 90 , the reaction was stirred for 6 hours incubation, naturally fell off the heating 80 , 600ml of cyclohexane was added, and stirring was continued to cool down to room temperature, solid precipitated, suction filtered, the filter cake washed with cold ethanol and dried under vacuum to give 233.6g.Yield: 78%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-oxoindoline-6-carboxylate, its application will become more common.

Reference:
Patent; Nanjing Aide Kai Teng biological medicine limited liability company; Wang, Xuegen; He, Lingyun; Li, Xiaojing; Li, Yiwen; Yu, Yang; Guo, Liqin; (8 pag.)CN105418483; (2016); A;,
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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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below., 1074-82-4

General procedure: The appropriate dibromoalkane derivative 2a-2e (11.9 mmol) was added slowly to a mixture of the starting material phthalimide potassium salt (1) (1g, 5.4 mmol) and anhydrous K2CO3 (0.82 g, 5.94 mmol) in acetone (15 mL). The reaction mixture was heated to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (50 mL) was added to the residue and the mixture was extracted with dichloromethane (30 mL ¡Á 3). The combined organic phases were washed with saturated aqueous NaCl, dried over Na2SO4, and filtered. The solvent was evaporated to dryness under reduced pressure. The crude product was purified on a silica gel chromatography using dichloromethane/acetone (50:1) as eluent to give the intermediates 3a-3e.

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.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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2913-97-5,Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

To a mixture of phthalimidoacetaldehyde (64 g, 0.34 mol) and trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (81.5 g, 0.38 mol) in benzene (600 ml) stirred for 15 min. under nitrogen was added dropwise a 45 percent solution of zinc chloride diethyl ether complex in dichloromethane (55.5 ml, 0.17 mol) at 0 ¡ãC. The reaction was allowed warm up to room temperature overnight. To the reaction mixture was added water (500 ml) and the resulting mixture was extracted with ethyl acetate (200 ml). The organic extract was washed successively with 1.0 N hydrochloric acid (2 x 200 ml) and brine (200 ml). The organic phase was dried (Na2SO4), filtered and the solvent evaporated invacuo which afforded a slowly crystallising oil (98 g). To the solid was added a mixture of ethyl acetate and diethyl ether (400 ml, 1:1) and the resulting precipitate was filtered off, washed with a small portion of diethyl ether and dried at 50 ¡ãC for 1 hour affording 59.8 g (69 percent) of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindote-1,3-dione as a solid. The filtrate was evaporated invacuo and the residue purified by column chromatography on silica gel (1 L) using a mixture of ethyl acetate and heptane (1:2) as eluent. Pure fractions were collected and the solvent evaporated invacuo to almost dryness, the solid was filtered off and dried invacuo at 50 ¡ãC for 16 h affording an additional 15 g (17 percent) of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.1H-NMR (300 MHz, CDCl3) delta 2.61 (d, 2H), 3.85 (dd, 1H), 4.18 (dd, 1H), 4.76 (m, 1H), 5.43 (d, 1H), 7.28 (d, 1H), 7.69 – 7.77 (m, 2H), 7.84 – 7.88 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(2-Oxoethyl)phthalimide, its application will become more common.

Reference:
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214325; (2005); B1;,
Indoline – Wikipedia,
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These common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, 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. 1127-59-9

General procedure: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.17 (Z)-2-(7-Methyl-2-oxoindolin-3-ylidene)-N-(p-tolyl)hydrazinecarbothioamide (3-17) Yield 73percent; m.p.: 247-249 ¡ãC; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.82 (s, 1H, NNH), 11.32 (s, 1H, NH), 10.74 (s, 1H, SCNH), 7.63 (d, 1H, J = 7.2 Hz, Ar1-H4), 7.50-7.48 (d, 2H, J = 8.0 Hz, Ar2-H3 and Ar2-H5), 7.25-7.19 (m, 3H, J = 7.6 Hz, Ar1-H6, Ar2-H2 and Ar2-H6), 7.03 (t, 1H, J = 7.6 Hz, Ar1-H5), 2.34 (s, 3H, Ar2-CH3), 2.248 (s, 3H, Ar1-CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.2, 163.1, 141.0, 135.9, 135.3, 132.5, 132.5, 128.8, 125.5, 122.3, 120.4, 119.6, 118.8, 20.6, 15.9; IR: (KBr, nu/cm-1), 3302 (NN-H), 3164 (CON-H), 3063 (Ar-H), 1693 (-CONH-), 1626 (C=N), 1585 and 1478 (Ar-C=C), 1211 (C=S), 1135 (N-N); Elemental analysis calculated for C17H16N4OS, C: 62.94, H: 4.97, N: 17.27, found C: 62.70, H: 5.15, N: 17.28; ESI-MS m/z: 323.1, [M – H]-.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1127-59-9.

Reference:
Article; Zhang, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
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These common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-dione, 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. 52351-75-4

General procedure: 2-Acetoxy-4?-methoxyacetophenone(5b) (779 mg, 3.74 mmol) in EtOH (8.20 mL) was added to a solution of compound 4a (500 mg,3.40 mmol) in 10N NaOH (3.0 mL) and EtOH (800 L) at 85 C. After the mixture was stirred at 85 Cfor 1 h, H2O (10.0 mL) was added to the mixture at 0 C. The mixture was acidified to pH 1 with 1N HCl.The precipitate was collected by filtration and washed with H2O and EtOH to give the title compound 6bas a yellow solid (742 mg, 74%)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52351-75-4.

Reference:
Article; Yamamoto, Koki; Okazaki, Shiho; Ohno, Hiroaki; Matsuda, Fuko; Ohkura, Satoshi; Maeda, Kei-ichiro; Fujii, Nobutaka; Oishi, Shinya; Bioorganic and Medicinal Chemistry; vol. 24; 16; (2016); p. 3494 – 3500;,
Indoline – Wikipedia,
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A common compound: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 14192-26-8

To a stirred solution of methyl 2-oxoindoline-6-carboxylate (1.00 g, 5.23 mmol) in acetic anhydride (10.9 mL, 1 15 mmol) was added (triethoxymethyl)benzene (3.55 mL, 15.7 mmol) and the mixture was stirred at 1 10 C for 4 h. The reaction mixture was cooled to rt and the resulting precipitate collected by filtration. The precipitate was washed with hexanes (100 mL) and dried in vacuo to afford the subtitle compound (?)-methyl 1-acetyl-3- (ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate as a beige solid (1.66 g, 82%); Rl 2.61 min (Method 1); m/z 366 (M+H)+ (ES+).

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, 14192-26-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESPIVERT LIMITED; WALTERS, Iain; BIRCH, Louise; HILL-COUSINS, Joseph; COLLINGWOOD, Stephen, Paul; STEVENSON, Christopher, Scott; (126 pag.)WO2017/109513; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem