Day: November 4, 2020

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

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.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

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

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

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; US5017579; (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.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.

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

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, 78593-33-6, , I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Sanofi; US5017579; (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.78593-33-6, 3-Bromocinnoline it is a common compound, a new synthetic route is introduced below.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%

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

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

Cinnolin-4(1H)-one (5.0 g, 34.24 mol) was added to the K2CO3 ( 7.08 g, 51.36 mol) and 3- bromoprop-1-yne (3.11 mL, 41.09 mol) in ACN (20 mL) and the mixture stirred at 80 C for 4-8 h then reaction mixture was cool to rt. The mixture was concentrated, diluted with H2O (30 mL), and extracted with EtOAc (3 ¡Á 50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. Flash chromatography gave 4-(prop-2-yn-1-yloxy)cinnoline (13a). Synthesis of 4-(prop-2-yn-1-yloxy)cinnoline (4a). Yield (2.60 g, 65.5%). m.p. 100-110 C. Colourless solid.1H NMR (400 MHz, CDCl3) delta 8.34 (dd, J = 1.2, 1.2 Hz, 1H, Ar), 7.81-7.77 (m, 2H, Ar), 7.60 (d, J = 8.8 Hz, 1H, Ar), 7.46 (t, J = 8.0 Hz,1H, Ar), 5.14 (d, J = 2.4 Hz, 1H, -OCH2), 2.51 (t, J = 2.4 Hz, 1H, Alky). 13C NMR (100 MHz, CDCl3) delta 171.2, 140.6, 140.1, 134.0, 126.0, 125.2, 124.6, 115.1, 76.0, 75.7, 46.2. ESI-MS: m/z 185.27 [M+H]+. Anal. Calc. (C11H8N2O) C: 71.73; H: 4.38; N: 15.21. Found C: 71.80; H: 4.04; N: 15.28%.

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
Article; Boda, Sathish Kumar; Bommagani, Mohan Babu; Chitneni, Prasad Rao; Mokenapelli, Sudhakar; Yerrabelli, Jayaprakash Rao; Synthetic Communications; (2020);,
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. 21905-86-2, C9H6N2O2, Here is a downstream synthesis route of the compound. 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, Cinnoline-4-carboxylic acid, , 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