Category: cinnoline

3-Bromocinnoline, 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%

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 3-Bromocinnoline reaction routes.

Reference£º
Patent; Sanofi; US4994474; (1991); A;,
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.875-66-1, Cinnolin-4-ol it is a common compound, a new synthetic route is introduced below.875-66-1

875-66-1, a. 4-Chloro-8-nitroquinoline (6a). This intermediate was prepared from 4-chloroquinoline (obtained by treating 4-hydroxyquinoline with [POC13] as [ DESCRIBED BY GOULEY, R. W., ET AL. , J. AMER. CHEM. SOC., 1947, 69, 303-306.4-] Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below 15 C. Then the solution was cooled and maintained at-15 C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g of 6a, in 59 % yield; m. p. = [128-129 C] (lit. m. p. = [129-130 C) ; IH] NMR [(CDC13)] [8] 7.67 (d, [1H,] J=4. 5), 7.75 (dd, 1H, J=8. 6 [HZ,] J=7. 6), 8.10 (dd, 1H, J=7. 6, J=1. 3), 8. 48 (dd, 1H,. [J=8.] [6,] J=1.3), 8.94 (d, 1H, J=4. 5); [13C] NMR [(CDC13)] [8] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1.

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; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
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.78593-33-6, 3-Bromocinnoline it is a common compound, a new synthetic route 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)

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 3-Bromocinnoline reaction routes.

Reference£º
Patent; Sanofi; US4957925; (1990); 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

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).

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; 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

Cinnolin-4(1H)-one, 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. 18514-84-6

To a solution of cinnolin-4(lH)-one in DMF (0.1 M) was added K2CO3 (1.2 eq) and methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 Al, 1 eq). The mixture was stirred and heated tolOO 0C for Ih. After cooling to RT the solvent was removed under reduced pressure and the residue was partitioned between DCM and H2O. The organic phase was washed with brine, dried (Na2SO4) and filtered and the solvent was removed under reduced pressure. The product was isolated by flash chromatography on silicagel, using a gradient of DCM/MeOH (from 0% to 10% MeOH in 10 CV). The 2-[4-fiuoro-3- (methoxycarbonyl)benzyl]cinnolin-2-ium-4-olate was eluted after the title compound.MS (ES) Ci8Hi3FN2O3 requires: 312, found: 313 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis, 18514-84-6, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/27730; (2009); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

3-Bromocinnoline, 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%

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 3-Bromocinnoline reaction routes.

Reference£º
Patent; Sanofi; US5147878; (1992); A;,
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

To a suspension of NaH (60% in mineral oil, 0.099 g, 2.46 mmol) in DMF (5 mL) was added cinnolin-4-ol (prepared from 2-aminoacetophenone according to the procedures described in U. S. Patent No. 4,620, 000), 0. 300 g, 2.05 mmol) in DMF (2 mL) dropwise. The reaction mixture was warmed at 40 C and stirred for 30 minutes. After cooling, N-phenyltrifluoromethanesulfonimide (0.880 g, 2.46 mmol) in DMF (2 mL) was added, and the reaction mixture was stirred at room temperature for 1 hour. 1-Boc piperazine (0.765 g, 4.11 mmol) was added to the mixture. The reaction was stirred at 80 C for 4 hours. After cooling, the mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated. The residue was purified by column chromatography (1: 1 to 1: 3 hexanes/EtOAc) to give 4- Cinnolin-4-yl-piperazine-l-carboxylic acid tert-butyl ester (0.246 g, 38%) as a yellow oil. 1H NMR (CDC13, 400 MHz) 8 8. 91 (s, 1H), 8. 47 (d, J= 8.4 Hz, 1H), 7.97 (d, J= 8. 4 Hz, 1H), 7.80 (t, J= 7.2 Hz, 1H), 7.69 (t, J= 7.2 Hz, 1H), 3.74 (m, 4H), 3. 34 (m, 4H), 1.51 (s, 9H). LCMS (APCI+) tnlz 315 [M+H]’ ; Rt = 2.14 minutes.

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; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics

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. 875-66-1, Cinnolin-4-ol. 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.875-66-1

a. 4-Chloro-8-nitroquinoline (6a). This intermediate was prepared from 4-chloroquinoline (obtained by treating 4-hydroxyquinoline with [POC13] as [ DESCRIBED BY GOULEY, R. W., ET AL. , J. AMER. CHEM. SOC., 1947, 69, 303-306.4-] Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below 15 C. Then the solution was cooled and maintained at-15 C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g of 6a, in 59 % yield; m. p. = [128-129 C] (lit. m. p. = [129-130 C) ; IH] NMR [(CDC13)] [8] 7.67 (d, [1H,] J=4. 5), 7.75 (dd, 1H, J=8. 6 [HZ,] J=7. 6), 8.10 (dd, 1H, J=7. 6, J=1. 3), 8. 48 (dd, 1H,. [J=8.] [6,] J=1.3), 8.94 (d, 1H, J=4. 5); [13C] NMR [(CDC13)] [8] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1.

The chemical industry reduces the impact on the environment during synthesis, 875-66-1, , I believe this compound will play a more active role in future production and life.

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

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. 875-66-1, Cinnolin-4-ol. 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.875-66-1

a. 4-Chloro-8-nitroquinoline (6a). This intermediate was prepared from 4-chloroquinoline (obtained by treating 4-hydroxyquinoline with [POC13] as [ DESCRIBED BY GOULEY, R. W., ET AL. , J. AMER. CHEM. SOC., 1947, 69, 303-306.4-] Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below 15 C. Then the solution was cooled and maintained at-15 C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g of 6a, in 59 % yield; m. p. = [128-129 C] (lit. m. p. = [129-130 C) ; IH] NMR [(CDC13)] [8] 7.67 (d, [1H,] J=4. 5), 7.75 (dd, 1H, J=8. 6 [HZ,] J=7. 6), 8.10 (dd, 1H, J=7. 6, J=1. 3), 8. 48 (dd, 1H,. [J=8.] [6,] J=1.3), 8.94 (d, 1H, J=4. 5); [13C] NMR [(CDC13)] [8] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1.

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

3-Bromocinnoline, 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

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%

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 3-Bromocinnoline reaction routes.

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