Month: May 2021

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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. .1.54 2-((2-(2-(Butan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (2C) White powder, mp 135-142 C, 87% yield; 1H NMR (400 MHz, CDCl3): delta 1.08-1.12 (t, 3H, CH3), 2.20 (s, 3H, CH3), 2.27-2.31 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.76 (bs, 2H, Ar), 7.86-7.87 (m, 2H, Ar).

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; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 19727-83-4

To an oven dried flask equipped with a stir bar cooled under argon was added 6-nitroindoline (2.0 grams, 12.2 mmol) and 61.0 mL of anhydrous drichloromethane. While stirring at 0 C 2- methoxyacetyl chloride (1.3 mL, 14.6 mmol) was added followed by triethylamine (2.2 mL, 16 mmol). The reaction slowly warmed to room temperature. Once complete, determined by LCMS, the reaction was quenched with water, and the organic material extracted using dichloromethane. The aqueous material was washed with dichloromethane twice. The combined organic material was washed with NaHC03 (sat.), brine, dried with Na2S04, filtered and concentrated. The crude material was then used without further purification.

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 19727-83-4.

Reference:
Patent; MUSC FOUNDATION FOR RESEARCH DEVELOPMENT; U.S. DEPARTMENT OF VETERANS AFFAIRS; LINDSEY, Christopher, C.; BEESON, Craig, C.; SCHNELLMANN, Rick, G.; (51 pag.)WO2018/85491; (2018); A1;,
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Indoline | C8H9N – PubChem

Application of 552330-86-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromoisoindolin-1-one (636 mg,3.0 mmol), 1D (800 mg, 3.0 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), Xantphos (52 mg, 0.09 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in dioxane (60 mE) was heated to 1000 C. for 4 h. After that time, the mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel (1%-10% EtOAc in pet. ether) to afford 5A (400 mg, 34%) as a yellow solid: ?H NMR (400 MHz, DMSO-d5) oe8.71 (s, 1H), 8.61 (d, J=8.4 Hz, 1H), 8.07 (t, J=8.4 Hz, 1H),8.0 (d, J=7.6 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 7.76 (d, J=3.2 Hz, 2H), 5.17 (s, 2H), 4.11-4.04 (m, 1H), 1.14-1.11 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 396.1, 398.1 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 446292-08-6 as follows. Computed Properties of C22H19N3O6

100 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I), 1000 ml Methanol and 119 g methyl amine were added to RBF at 25 C. to 35 C. The reaction was heated to 60 C. to 65 C. for 1-2 hours. To the reaction mass formic acid (15 g) was added till to pH 5.5 to 6.0 and maintained for 30 minutes. The reaction mass was cooled to 45 to 50 C. and maintained for 30 minutes. The reaction mass was cooled to 25 to 35 C. and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml*2) afforded the formate salt of (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one of Formula (JF).

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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 compound [3-7]a-i (0.01mole) and thionyl chloride (0.01mole) placed in dry benzene (10 ml.) and refluxed for 7 hours. The excess of thionyl chloride and benzene were removed under vacuum after cooling .

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Samir, Ali H.; Saeed, Ruwaidah S.; Matty, Fadhel S.; Oriental Journal of Chemistry; vol. 34; 1; (2018); p. 286 – 294;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2058-72-2, 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 2058-72-2 as follows.

General procedure: Dialkyl acetylenedicarboxylate 2 (1 mmol) was added to a magnetically stirred 5 mL flat bottom flask containing hydrazine hydrate (1 mmol) and H2O (2 mL) at room temperature. After 10 min, isatin 1(1 mmol) malononitrile (1 mmol) and NaCl (20 mol %) were added and the reaction heated at 50 C for 10 min. After completion of the reaction (monitoring by TLC), the reaction mixture was filtered and the precipitate washed with water and then ether to afford the pure products 3a-h. Methyl 6?-amino-5-bromo-5?-cyano-1-methyl-2-oxo-1?H-spiro-[indoline-3,4?-pyrano[2,3-c]pyrazole]-3?-carboxylate (3g): Yellow powder; yield: 0.25 (80%); m.p. 275-276 C; IR (KBr): 3432, 3307, 3173 (NH2and 2NH), 2200 (C?N), 1720 (CO2Me), 1698 (NCO), 1638, 1602, 1487 (Ar), 1190 (C-O) cm-1; 1H NMR: delta3.35 (3H, s, NCH3), 3.48 (3H, s, OCH3), 7.09 (1H, d, 3JHH= 7.6 Hz, CH6of Ar), 7.31 (1H, s, CH4of Ar), 7.44 (2H, s, NH2), 7.50 (1H, d, 3JHH= 7.2 Hz, CH7of Ar), 14.05 (1H, s, NH) ; 13C NMR: delta26.5 (NCH3), 47.0 (Cspiro), 52.0 (OCH3), 55.5 (C-CN), 99.8 (C3?), 110.2 (CH7), 114.3 (C-Br), 117.8 (CN), 126.4 (CH4), 128.3 (C3a), 131.3 (CH6), 135.2 (C-CO2Me), 142.9 (C7a), 155.9 (OCN), 157.6 (CO2Me), 161.2 (C-NH2), 175.4 (C=O of isatin); MS (EI, 70 eV): m/z (%) = 430 [M+], 403, 287, 142, 101, 83, 59. Anal. calcd for C17H12BrN5O4(430.21): C, 47.46; H, 2.81; N, 16.28; found: C, 47.39; H, 2.74; N, 16.37%.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Journal of Chemical Research; vol. 39; 8; (2015); p. 464 – 466;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5, 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 132898-96-5 as follows.

Example 4 (S)-5-(2-Phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (10). To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0 C. The mixture was stirred at 0 C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0 C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9 C. 1H NMR (300 MHz, CDCl3) delta 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Washington University in St. Louis; US2009/68105; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 2058-72-2

To a sol. of 5-bromo-1-methyl-1 H-indole- 2,3-dione (3.60 g, 15.0 mmol) in THF (100 mL) are added sequentially at rt trifluoromethyl)trimethylsilane (4.43 mL, 30.0 mmol) and CsF (91.1 mg, 0.60 mmol). The resulting sol. is stirred at rt overnight. The mixture is quenched with cold water (100 mL). The mixture is extracted with EtOAc (3 x 100 mL). The comb. org. layers are washed with brine (100 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure. Purification of the residue by automated FC (Combiflash, column 80 g, flow 60 mL/min, EtOAc / heptane 0:100 ? 20:80) yields the tri methyl si lyl -protected product. To a sol. of this isolated compound in MeOH (50 mL) is added aq. 2M HCI (40 mL). The resulting sol. is stirred at rt for 2 h. The reaction is diluted with CH2CI2 (100 mL). The layers are separated and the aq. phase is extracted with CH2CI2 (2x 50 mL). The comb. org. layers are washed with brine (1 x 50 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure to yield the crude title product. LC-MS: tR = 0.79 min (conditions 3).

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:
Patent; ACTELION PHARMACEUTICALS LTD; SIEGRIST, Romain; HEIDMANN, Bibia; STAMM, Simon; GATFIELD, John; BEZENCON, Olivier; WO2015/186056; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 65826-95-1, 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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 23 6,7-Dimethoxy-4-(5-methyl-2,3-dihydro-indol-1-yl)-quinazoline Utilizing a procedure analogous to that described in Example 1, this product was prepared in 94% yield from 5-methyl-indoline (1.1 eq.) and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 180-181 C.; GC/MS: 321 (M+); anal. RP18-HPLC RT: 4.37 min.).

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, 5-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H9NO2

General procedure: To a solution of DHEA (0.5 mmol, 1.0 eq) and isatin derivative(0.75 mmol, 1.5 eq) in EtOH (10 mL) was added Al2O3/KF (0.5 mmol,1.0 eq), the resulting mixture was stirred at reflux temperature for 6 h.Upon completion of the reaction indicated by the TLC, the mixture wasfiltered and the solid was washed with dichloromethane (DCM) forseveral times. The filtrate was then evaporated under vacuum, followedby addition of DCM and H2O. The mixture was then acidified with 4MHCl (pH=1-2). The aqueous layer was washed with DCM for severaltimes. The combined organic layers were then dried over Na2SO4 andevaporated under vacuum to the crude product, which was then subjectedto column chromatography, affording the corresponding product.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Yan-Tao; Du, Shuzhang; Wang, Song; Jia, Xuedong; Wang, Xiaojuan; Zhang, Xiaojian; Steroids; vol. 151; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem