7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

Base Information

Chemical Name:7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline
CAS No.:957110-22-4
Molecular Formula:C₂₃H₂₅N₃O₇
Molecular Weight:455.467
Hs Code.:

Synonyms:7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

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Chemical Property of 7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

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Technology Process of 7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

There total 22 articles about 7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 957110-20-2
5,8-dimethoxy-4-(2-nitrophenyl)-7-quinolinecarboxylic acid

: 122-07-6
N-(methyl)aminoacetaldehyde dimethyl acetal

: 957110-22-4
7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1021/jo7017813

Reference yield:

: 957110-12-2
3-acetamido-2,5-dimethoxy-2-(nitrobenzoyl)-acetanilide

: 957110-22-4
7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

Guidance literature:: Multi-step reaction with 8 steps

1.1: 52 percent / polyphosphoric acid / 5 h / 75 °C

2.1: 70 percent / triethylamine / 0.5 h / -20 °C

3.1: 87 percent / formic acid; triethylamine / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 2 h / 0 - 60 °C

4.1: glacial acetic acid; sulfuric acid / H₂O / 2 h / Heating

5.1: sodium nitrite / H₂O / 0 - 5 °C

5.2: 265 mg / H₂O / 1.25 h / 45 - 50 °C

6.1: sulfuric acid / 3.5 h / 60 - 70 °C

7.1: 43 mg / H₂O / 2 h / 120 °C

8.1: 87 percent / EDC*HCl / CH₂Cl₂ / 15 h / 20 °C

With formic acid; PPA; sulfuric acid; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide; 1.1: Knorr cyclization / 5.2: Sandmeyer reaction;
DOI:10.1021/jo7017813

Reference yield:

: 957110-13-3
7-acetamido-5,8-dimethoxy-4-(2-nitrophenyl)-2(1H)-quinolinone

: 957110-22-4
7-[N-(2,2-dimethoxyethyl)-N-methyl]-carboxamide-5,8-dimethoxy-4-(2-nitrophenyl)quinoline

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / triethylamine / 0.5 h / -20 °C

2.1: 87 percent / formic acid; triethylamine / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 2 h / 0 - 60 °C

3.1: glacial acetic acid; sulfuric acid / H₂O / 2 h / Heating

4.1: sodium nitrite / H₂O / 0 - 5 °C

4.2: 265 mg / H₂O / 1.25 h / 45 - 50 °C

5.1: sulfuric acid / 3.5 h / 60 - 70 °C

6.1: 43 mg / H₂O / 2 h / 120 °C

7.1: 87 percent / EDC*HCl / CH₂Cl₂ / 15 h / 20 °C

With formic acid; sulfuric acid; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In dichloromethane; water; N,N-dimethyl-formamide; 4.2: Sandmeyer reaction;
DOI:10.1021/jo7017813