Tag: M.W=100-200

These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-one, 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. Recommanded Product: 1-Methylindolin-2-one

Step 2; Preparation of 1-methyl-5-nitro-1,3-dihydro-indol-2-one; 1-Methyl-1,3-dihydro-indol-2-one (Step 1, 2.10 g, 14.3 mmol) is added in portions to 70% nitric acid (10 ml) at -10 C. After the addition is complete, the reaction is allowed to warm to room temperature and then stirred for 5 hours. The mixture is diluted with ice water and the resulting precipitate filtered, washed with water, and dried under a vacuum to give the title compound as a brown solid. HPLC r.t. 3.97 min; MS for C9H8N2O3 m/Z 193.9(M+H)+.

The synthetic route of 1-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Luehr, Gary; Gordeev, Mikhail; US2006/229348; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7223-50-9, A common heterocyclic compound, 7223-50-9, name is N-Propargylphthalimide, molecular formula is C11H7NO2, 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 a terminal alkyne (2.0 mmol), paraformaldehyde (180.2 mg, 2.0 mmol), amine (2 mmol) and Pt/TiO2 (5.0 mg, 0.25 mol%) loaded in distilled H2O (3 mL) and heated under microwave condition at 140 C and 250 W for appropriate reaction time (the reaction was monitored by TLC). After the completion of the reaction, the mixture was allowed to cool down and then extracted with EtOAc (3*20 mL). The combined organic extracts were dried (MgSO4) and fltered. The solvent was evaporated under reduced pressure and the resulting crude product was purifed by column chromatography (silica gel) to obtain the corresponding products 4a-4l.

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; Mohamed, Yasser M. A.; El Nazer, Hossam A.; Solum, Eirik Johansson; Chemical Papers; vol. 73; 2; (2019); p. 435 – 445;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-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. HPLC of Formula: C8H4ClNO2

Nitrogen protected, cooled to -15 C, 0.60 g (2.5 mmol) of 3-n-butyl-5-chloro-3-hydroxyisoindolin-1-one and 3-n-butyl-6-chloro-3 -A mixture of hydroxyisoindolin-1-one was dissolved in 30 ml of DCM, and then 2.9 g (25.0 mmol) of triethylsilane and 1.1 g (7.5 mmol) of boron trifluoride ether solution were added, and the temperature was returned to room temperature, and the reaction was performed. Overnight, TLC showed the reaction was complete.The reaction solution was poured into a 5% sodium solution, extracted with DCM, dried, concentrated, and subjected to silica gel column chromatography. A mixed eluent of ethyl acetate and petroleum ether was used as the eluent (the volume ratio of ethyl acetate and petroleum ether was 1: 1), get:3-n-butyl-5-chloroisoindolin-1-one (A) (small polar point, first eluted component), yield 35.7%.3-n-butyl-6-chloroisoindolin-1-one (B) (a point of great polarity, the second elution component), with a yield of 37.5%.

The synthetic route of 5-Chloroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aisite (Chengdu) Bio-pharmaceutical Co., Ltd.; Fu Jiasheng; Chen Xing; Yang Youzhe; Chen Xiaogang; Chen Jiachang; Sun Jingxiong; Gan Man; Guo Peng; (41 pag.)CN110563631; (2019); A;,
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Reference of 1914-02-9, 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. 1914-02-9, name is 3,3-Dimethylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (133 mg, 0.703 mmol) in 7 mL DMF, triethylamine (127 mu^ 0.912 mmol) and HATU (319 mg, 0.839 mmol) were added. After stirring at room temperature for 5 min, 3,3-dimethylindoline (97.2 mg, 0.660 mmol) was added. After stirring at room temperature for 4 h, the mixture was extracted with AcOEt and brine. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give (S)-tert-butyl (l-(3,3-dimethylindolin-l-yl)-l-oxopropan-2-yl)carbamate (204 mg) as a white solid. LCMS m/z = 319.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 1.358 (s, 3H), 1.364 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H), 1.45 (s, 9H), 3.78 (d, J = 10.0 Hz, 1H), 4.00 (d, J = 10.0 Hz, 1H), 4.54-4.61 (m, 1H), 5.46 (d, J = 8.5 Hz, 1H), 7.07-7.10 (m, 1H), 7.15-7.16 (m, 1H), 7.20-7.24 (m, 1H), 8.17 (d, J = 8.1 Hz, 1H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
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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 340702-10-5 as follows. Computed Properties of C8H6FNO

[0128] Step c: To a 0 C suspension of 6-fluoroisoindoline-l-one (8.0 g, 5.3 mmol) in concentrated H2S04was added drop-wise a pre-cooled mixture of concentrated H2S04(26 mL) and nitric acid (6 mL) while keeping the reaction mixture below 5 C. After addition, the reaction mixture was slowly warmed to room temperature during overnight. Ice (50 g) was added to the mixture and the solid was collected and dried, then washed with MTBE (50 mL) and ethyl acetate (50 mL) to give the desired product as a light yellow solid (5.1 g, 50%). MS: (ES) m/z calculated for C8H6FN203[M + H]+197, found 197.

According to the analysis of related databases, 340702-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan, Reddy; MALATHONG, Viengkham; MCMAHON, Jeffrey; TANKAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; MALI, Venkat; (104 pag.)WO2017/87610; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-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 89-40-7, SDS of cas: 89-40-7

Add 112.8 g of stannous chloride dihydrate and 70 mL of concentrated hydrochloric acid to a 500 mL three-necked flask, and stir until completely dissolved.19.2 g of 4-nitrophthalimide was added, and the reaction was stopped after reacting at 40 C for 1 h.The reaction solution was suction filtered to obtain a filter residue, and the filter residue was washed twice with 50 mL of concentrated hydrochloric acid and then dried.After washing twice with 50 mL of ethyl acetate, a second suction filtration was performed.The filter residue obtained by the second suction filtration was dried to obtain 14.9 g of 4-aminophthalimide yellow powder, and the yield was 92%.

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-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WUYI UNIV; Wuyi University; ZHAO JUAN; Zhao Juan; (7 pag.)CN107778211; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 56341-37-8, These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

NBS (5.8 g, 32.8 mmol) was added to a solution of 6-chlorooxiindole (5.0 g, 29.8 mmol) in acetonitrile (50 mL) at -10 00 . The reaction mixture was stirred at room temperature for 3 h. The reaction was monitored by LC-MS. The reaction mixture was evaporated to dryness and was extracted with ethyl acetate. The ethyl acetatelayer was washed with water and dried over anhydrous Na2SO4 and concentrated under reduced, which was purified by trituration with n-hexane to yield title compound (7.0 g, 95.8 %) as a brown solid. LOMS: (M-H) = 244.9; 1H NMR: (DMSO-d6, 300MHz) 6 10.61(s, 1H), 7.56(s, 1H), 6.98(s, 1H), 3.51(s, 2H).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 37a; Preparation of intermediate E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester; To a mixture of 6-chlorooxindole (4.58 g, 20 mmol) and 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10 g, 26 mmol) in methanol (50 mL) was added piperidine (2.56 mL, 26 mmol) dropwise. The mixture was then heated at 100 C. for 3 h. After cooled to 4 C., the mixture was filtered and the precipitate was collected, dried to give the title compound as a bright yellow solid (12.4 g, 90%).

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

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

Example 13; Synthesis of 4-chloro-6-(1.3-dihvdro-2H-isoindol-2-yl)pyrimidin-2- amine (Intermediate 18); 4,6-Dichloropyrimidin-2-amine (1.12g), isoindoline (1.2ml), and triethylamine (1.63ml) in EtOH (33ml) are heated with stirring at 85 0C for 6 hours. The solvent is removed in vacuo, and the residual solid suspended in DCM (40ml) and dilute citric acid solution (30ml). The suspended solid is filtered off, washed with DCM and water, and dried to afford the title compound as a grey solid (1.573g, 93%). LCMS 247 [M+H]+, RT 3.05 mins (pH 2.5). 1H NMR 300 MHz (CDCI3) (delta ppm): 7.25 – 7.48 (4H, m), 6.58 (2H, s), 5.92(1H, s), 4.71 (4H, br d).

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA, S.A.; WO2008/31556; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2, 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 7147-90-2 as follows.

2-chloro-6-bromoquinoline (240 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol)5-chlorophthalimide (360 mg, 2 mmol), sodium carbonate (210 mg, 2 mmol),Acetonitrile (2 ml) was added to the dry reaction tube and suspended in an oil bath at 120 C for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 378 mg of colorless solid2- (2- (4- (6-bromoquinolyl) 2-piperazinyl) 1-ethyl) -5-chloroisoindole-1,3-dione,The yield was 76%.

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem