A new synthetic route of Cinnolin-4-ol

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,875-66-1,Cinnolin-4-ol,its application will become more common.

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

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,875-66-1,Cinnolin-4-ol,its application will become more common.

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

A new synthetic route of Cinnoline-4-carboxylic acid

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

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

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).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

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

The origin of a common compound about 78593-33-6

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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 50ml of dimethylsulphoxide was stirred and heated at -20 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%

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

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

Some scientific research about 3-Bromocinnoline

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-Bromocinnoline,78593-33-6,its application will become more common.

78593-33-6 A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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.

Starting material 1-A (11.8 g, 40 mmol), starting material 1-B (16.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol), and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. Then, the reaction mixture was cooled to room temperature, 300 ml of water was added to isolate the organic layer, and the water layer was extracted twice with 250 ml of dichloromethane. The extracted organic layer was stirred with MgSO4 to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The resulting solid was subjected to column chromatography using, as an eluent, dichloromethane and normal hexane to obtain 5.6 g of Intermediate 1-C at the yield of 33%. MS (MALDI-TOF) m/z: 424 [M]+

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-Bromocinnoline,78593-33-6,its application will become more common.

Reference£º
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Myeongsuk; Ye, Jimyoung; Yoo, Byeongwook; Cho, Illhun; Kang, Sunwoo; Kim, Sunjae; Jeong, Jaeho; (112 pag.)US2020/99001; (2020); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

A new synthetic route of 3-Bromocinnoline

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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%

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

Reference£º
Patent; Sanofi; US5147878; (1992); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Some scientific research about Cinnolin-4(1H)-one

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18514-84-6,Cinnolin-4(1H)-one,its application will become more common.

18514-84-6 A common heterocyclic compound, 18514-84-6,Cinnolin-4(1H)-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.

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).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18514-84-6,Cinnolin-4(1H)-one,its application will become more common.

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

Some scientific research about 3-Bromocinnoline

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-Bromocinnoline,78593-33-6,its application will become more common.

78593-33-6 A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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.

Starting material 1-A (11.8 g, 40 mmol), starting material 1-B (16.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol), and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. Then, the reaction mixture was cooled to room temperature, 300 ml of water was added to isolate the organic layer, and the water layer was extracted twice with 250 ml of dichloromethane. The extracted organic layer was stirred with MgSO4 to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The resulting solid was subjected to column chromatography using, as an eluent, dichloromethane and normal hexane to obtain 5.6 g of Intermediate 1-C at the yield of 33%. MS (MALDI-TOF) m/z: 424 [M]+

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-Bromocinnoline,78593-33-6,its application will become more common.

Reference£º
Patent; SAMSUNG DISPLAY CO., LTD.; Kim, Myeongsuk; Ye, Jimyoung; Yoo, Byeongwook; Cho, Illhun; Kang, Sunwoo; Kim, Sunjae; Jeong, Jaeho; (112 pag.)US2020/99001; (2020); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

Some scientific research about 3-Bromocinnoline

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

78593-33-6 A common heterocyclic compound, 78593-33-6,3-Bromocinnoline, 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, 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)

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78593-33-6,3-Bromocinnoline,its application will become more common.

Reference£º
Patent; Sanofi; US5147878; (1992); A;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

A new synthetic route of 4-Aminocinnoline-3-carboxamide

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38024-35-0,4-Aminocinnoline-3-carboxamide,its application will become more common.

A common heterocyclic compound, 38024-35-0,4-Aminocinnoline-3-carboxamide, 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. 38024-35-0

To a suspension of 4-aminocinnoline-3-carboxamide (3.5 g, 18.60 mmol) in DCM (10 ml) was added POCI3 (43.3 ml, 465 mmol) followed by triethylamine (7.78 ml, 55.8 mmol). The mixture was refluxed for 7 h. The reaction was then allowed to cool to 11 and conc, in vacuo. The crude residuewas then carefully treated with saturated aqueous NaHCO3 at 0 C. A precipitate formed which was collected via vacuum filtration. The filter cake washed with water (-i00 ml,), collected, and driedvacuo to provide the title compound as a grey solid 4-aminocinnoiine-3-carbonitriie., 38024-35-0

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38024-35-0,4-Aminocinnoline-3-carboxamide,its application will become more common.

Reference£º
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

The origin of a common compound about 21905-86-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

A common heterocyclic compound, 21905-86-2,Cinnoline-4-carboxylic acid, 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 63f Synthesis of Cinnoline-4-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide (Compound 63f) The procedure in Example 63d step 3 was followed using cinnoline-4-carboxylic acid. The reaction was stirred at RT for 1 day and at reflux for 1 day. Purification by chromatography (SiO2, 5-8% MeOH/CH2Cl2 with 1% NH4OH) afforded the title compound as a foam (63 mg, 0.125 mmol, 44%). The structure was confirmed by NMR and mass spectrometry. MS m/z 505 (M++H).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21905-86-2,Cinnoline-4-carboxylic acid,its application will become more common.

Reference£º
Patent; Denny, William Alexander; Hutchings, Richard H; Johnson, Douglas S; Kaltenbronn, James Stanely; Lee, Ho Huat; Leonard, Daniele Marie; Milbank, Jared Bruce John; Repine, Joseph Thomas; Rewcastle, Gordon William; White, Andrew David; US2004/44057; (2004); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics