Day: September 28, 2020

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

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

EXAMPLE 5 n-Propyl Cinnoline-4-carboxylate (5) A suspension of 870 mg of 1, and 850 mg of carbonyidimidazole (CDII) in 30 ml of tetrahydrofuran (THF) was stirred at room temperature until CO2 evolution ceased (ca. 30 minutes). After being stirred for 2 hours, the resulting mixture was treated with 320 mg of dry nypropanol and 3 drops of a 0.1 M solution of sodium imidazole in THE. The mixture was held at room temperature overnight, then the solvent was evaporated and the residue was partitioned between water and ether. The etheral extract was washed with saturated sodium bicarbonate solution, then with brine, then dried (MgSO4) and stripped in a rotary evaporator. The residue was chromatographed over silica gel, using a 1:1 v:v mixture of cyclohexane and ethyl acetate as eluent, to give 5, as a yellow oil.

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; E. I. Du Pont de Nemours and Company; US4699651; (1987); 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-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

(0509) Compound 110 (292 mg, 2.00 mmol) was refluxed in POCl3 overnight. It was cooled to room temperature and poured into ice water, neutralized with Na2C03. The precipitation was filtered out and washed with water, dried by pulling air through. Product was obtained as light yellow solid. (0510) (243mg, 74%). 1H NMR (400 MHz, chloroform-i/) delta 9.35 (s, 1H), 8.57 (ddd, J= 8.5, 1.4, 0.7 Hz, 1H), 8.20 (ddd, J= 8.2, 1.6, 0.7 Hz, 1H), 7.97 – 7.83 (m, 2H).

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; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang Hubert; ZHANG, Shuting; HU, Zhenyi; (114 pag.)WO2019/89648; (2019); 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

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.

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; E. I. Du Pont de Nemours and Company; US4699651; (1987); 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

18514-84-6, 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.”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

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

(0509) Compound 110 (292 mg, 2.00 mmol) was refluxed in POCl3 overnight. It was cooled to room temperature and poured into ice water, neutralized with Na2C03. The precipitation was filtered out and washed with water, dried by pulling air through. Product was obtained as light yellow solid. (0510) (243mg, 74%). 1H NMR (400 MHz, chloroform-i/) delta 9.35 (s, 1H), 8.57 (ddd, J= 8.5, 1.4, 0.7 Hz, 1H), 8.20 (ddd, J= 8.2, 1.6, 0.7 Hz, 1H), 7.97 – 7.83 (m, 2H).

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; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang Hubert; ZHANG, Shuting; HU, Zhenyi; (114 pag.)WO2019/89648; (2019); A1;,
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

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]+

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; 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

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

(0509) Compound 110 (292 mg, 2.00 mmol) was refluxed in POCl3 overnight. It was cooled to room temperature and poured into ice water, neutralized with Na2C03. The precipitation was filtered out and washed with water, dried by pulling air through. Product was obtained as light yellow solid. (0510) (243mg, 74%). 1H NMR (400 MHz, chloroform-i/) delta 9.35 (s, 1H), 8.57 (ddd, J= 8.5, 1.4, 0.7 Hz, 1H), 8.20 (ddd, J= 8.2, 1.6, 0.7 Hz, 1H), 7.97 – 7.83 (m, 2H).

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; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang Hubert; ZHANG, Shuting; HU, Zhenyi; (114 pag.)WO2019/89648; (2019); A1;,
Cinnoline – Wikipedia
Cinnoline – an overview | ScienceDirect Topics