Category: cinnoline

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. 78593-33-6, 3-Bromocinnoline. 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.78593-33-6

Using the same procedure as that described above but from 3-bromocinnoline there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6% M.P.: 108 C. (isopropanol)

The chemical industry reduces the impact on the environment during synthesis, 3-Bromocinnoline, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Sanofi; US4957925; (1990); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

78593-33-6, A common heterocyclic compound, 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. 78593-33-6

(a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of 3-bromocinnoline, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%

The chemical industry reduces the impact on the environment during synthesis, 78593-33-6, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Sanofi; US4994474; (1991); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

21905-86-2, A common heterocyclic compound, 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. 21905-86-2

To a solution OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), cinnoline-4-carboxylic acid (25mg, 0.14 mmol), Et3N (0.06 mL, 0.43 MMOL) in DMF (3 mL, anhydrous) was added HATU (60mg, 0. 16MMOL) at room temperature. After 16 h the reaction mixture was poured into ice water, and the solid was collected by filtration. The solid was dissolved in CH2CI2, and dried over NA2SO4. Concentration in vacuo, and purification by preparative TLC (CH2CI2-MEOH, 9: 1) afforded the title compound as a light yellow powder. MS: 564 (M+).

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 Cinnoline-4-carboxylic acid reaction routes.

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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.21905-86-2, Cinnoline-4-carboxylic acid it is a common compound, a new synthetic route is introduced below.21905-86-2

A solution of cinnoline-4-carboxylic acid (183 mg, 1.02 mmol) in methylene chloride (20 ml) was reacted with EDCI (195 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min and then stirred, together with 4b-amino-9b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]-inden-10-one (250 mg, 0.85 mmol), overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO4 and concentrated in a vacuum. Purification by column chromatography (ethylacetate:n-hexane=1:1) afforded the title compound as a white solid (290 mg, 63%). [0846] 1H-NMR (300 MHz, CD3OD) delta 1.15 (d, J=6.8 Hz, 6H, CH3), 2.82 (sep, J=6.8 Hz, 1H, CH), 6.69 (s, 1H, ArH), 6.89 (d, J=7.8 Hz, 1H, ArH), 7.45 (d, J=7.9 Hz, 1H, ArH), 7.65 (m, 1H, ArH), 7.858.03 (m, 5H, ArH) 8.42 (d, J=8.0 Hz, 1H, ArH), 8.51 (d, J=8.4 Hz, 1H, ArH), 9.45 (s, 1H, ArH).

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R & D; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Jung, Young Sik; Lee, Chong Kgo; Kim, Hae Soo; Jeong, Hee Chun; Kim, Pil Ho; Han, Soo Bong; Shin, Jin Soo; Neyts, Johan; Thibaut, Hendrik Jan; US2014/114068; (2014); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnolin-4-ol, A common heterocyclic compound, 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. 875-66-1

875-66-1, Example 20: Synthesis of 1- [4- (5-FLUORO-2-METHOXYPHENYL)-2-HYDROXY-4-METHYL-2- TRIFLUOROMETHYLPENTYL]-LH-CINNOLIN-4-ONE To a suspension of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et AL., Tetrahedron, 2000,56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 ML) was added sodium ethoxide (21 wt. % solution in ethanol, 276 PL). After heating at 85C for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m. p. 122C-123C.

The chemical industry reduces the impact on the environment during synthesis, Cinnolin-4-ol, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnolin-4-ol, A common heterocyclic compound, 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. 875-66-1

Example 20: Synthesis of 1- [4- (5-FLUORO-2-METHOXYPHENYL)-2-HYDROXY-4-METHYL-2- TRIFLUOROMETHYLPENTYL]-LH-CINNOLIN-4-ONE To a suspension of 2- [2- (5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (216 mg) and cinnolin-4-ol (V. G. Chapoulaud et AL., Tetrahedron, 2000,56, pp. 5499-5507) (216 mg) in anhydrous ethanol (1.2 ML) was added sodium ethoxide (21 wt. % solution in ethanol, 276 PL). After heating at 85C for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 40% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (26 mg), m. p. 122C-123C.

The chemical industry reduces the impact on the environment during synthesis, Cinnolin-4-ol, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/63163; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnoline-4-carboxylic acid, A common heterocyclic compound, 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. 21905-86-2

EXAMPLE 42 2-(2-ethoxyethoxy)ethyl cinnoline-4-carboxylate (42) 1.07 g of CDIT was added to a mixture of 1.04 g of 1 in 70 ml of dry THF under nitrogen, the mixture was stirred at room temperature for 4 hours, 1.6 g of 2-(2-ethoxyethoxy)ethanol and 0.032 g of sodium methoxide were added and the mixture was stirred at room temperature over a weekend. Then the solvent was stripped, and the residue was dissolved in methylene chloride. The solution was washed with water, dried (MgSO4) and stripped of solvent. The residue was flash-chromatographed on silica gel, using a 1:4 v:v mixture of ethyl acetate and methylene chloride as eluent, to give 42, as a yellow oil., 21905-86-2

The chemical industry reduces the impact on the environment during synthesis, Cinnoline-4-carboxylic acid, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. 18514-84-6, C8H6N2O, Here is a downstream synthesis route of the compound. 18514-84-6

Intermediate 2: Preparation of 3-Bromo-l,4-dihydro-4-cinnolinone:Bromine (0.8 ml) in acetic acid (10 ml) was added to a mixture of cinnolin-4- one (1.5 g, 10.27 mmol), sodium acetate (1.51 g, 18.49 mmol) and acetic acid (15 ml) maintained at 100 0C and stirred at that temperature for Ih. The mixture was concentrated under reduced pressure to half the initial volume and poured into water. The precipitated solid was filtered, washed with water and dried under reduced pressure. Yield: 64%. 1H-NMR (delta ppm, CDCl3, 300 MHz): 13.87 (br. s, IH); 8.06 (d, J = 7.8, IH); 7.84-7.80 (m, IH); 7.61 (d, J = 8.7, IH); 7.49 (t, J = 7.8, IH).

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 Cinnolin-4(1H)-one reaction routes.

Reference£º
Patent; GLENMARK PHARMACEUTICALS, S.A.; WO2009/53799; (2009); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. 875-66-1, C8H6N2O, Here is a downstream synthesis route of the compound. 875-66-1

875-66-1, a. [4-CHLOROCINNOLINE] (9b). A mixture of 4-hydroxycinnoline (2.0 g, 13.7 mmol), phosphorus oxychloride (1.94 mL, 20.5 mmol), and pyridine (0.33 mL, 4.1 mmol) in [CHLOROBENZENE] (50 mL) was refluxed for 1 hour. Then the mixture was cooled and the solvent evaporated under vacuum, water was added, and the mixture was neutralized with solid sodium bicarbonate and extracted with chloroform (3 x 100 mL), washed with water (3 x 100 mL), dried [(MGS04)] and evaporated under vacuum, giving 1.84 g, in 82 % yield; [MP] [76-77 C] (lit mp 78 [C)] [; IH] NMR [(CDC13)] [8] 7.91 (m, 2H), 8.20 (dd, 1H, [J=6.] 2, [J=2.] 1), 8.57 (dd, 1H, J=6. 6, J=1. 8), 9.34 (s, [1H)] ; [13C NMR (CDCL3) No. ] 123.0, 124.9, 130.2, 131.6, 132.3, 133.8, 134.9, 144.4.

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 Cinnolin-4-ol reaction routes.

Reference£º
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Cinnoline-4-carboxylic acid, A common heterocyclic compound, 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. 21905-86-2

1-(Ethoxycarbonyl)ethyl Cinnoline-4-carboxylate (32) A solution of 0.75 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 20 ml of benzene was added to a stirred suspension of 0.87 g of 1 in 30 ml of benzene at room temperature. After one hour of stirring, 1.36 g of ethyl 2-bromopropionate was added and the mixture was heated at reflux for 6 hours. The mixture was cooled, diluted with 25 ml of benzene, washed with water, 1 N aqueous sodium bicarbonate, and brine. It then was dried (MgSO4), the solvent was evaporated and the residue was chromatographed on silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 32, as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis, 21905-86-2, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; E. I. Du Pont de Nemours and Company; US4699651; (1987); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics