ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

Base Information

Chemical Name:ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate
CAS No.:1099474-22-2
Molecular Formula:C₂₀H₁₇Cl₂N₃O₃
Molecular Weight:418.279
Hs Code.:

Synonyms:ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

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Chemical Property of ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

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Technology Process of ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

There total 6 articles about ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate 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:

: 205646-85-1
(E)-2-(3-aminophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl)-propenonitrile

: 205646-86-2
ethyl (Z)-4,6-dichloro-3-[2-(3-aminophenyl)2-cyanoethenyl]-1H-indole-2-carboxylate

: 1099474-23-3
(E)-2-(3-aminophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl)-propenoic acid amide

: 1099474-22-2
ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

Guidance literature:: (E)-2-(3-aminophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl)-propenonitrile; ethyl (Z)-4,6-dichloro-3-[2-(3-aminophenyl)2-cyanoethenyl]-1H-indole-2-carboxylate; With sulfuric acid; water; acetic acid; at 90 ℃; for 2h;

With sodium hydroxide; In water; pH=5;

Reference yield:

: 205646-86-2
ethyl (Z)-4,6-dichloro-3-[2-(3-aminophenyl)2-cyanoethenyl]-1H-indole-2-carboxylate

: 1099474-22-2
ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

Guidance literature:: With sulfuric acid; acetic acid; at 50 ℃;
DOI:10.1021/op000286s

Reference yield:

: 103855-01-2
ethyl 2-[2-(3,5-dichlorophenyl)hydrazinylidene]propanoate

: 1099474-22-2
ethyl (Z)-4,6-dichloro-3-[(3-amino-2-aminophenyl)-3-oxo-1-propenyl]-1H-indole-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: polyphosphoric acid / toluene / 2 h / 95 - 100 °C / Inert atmosphere; Large scale

2.1: trichlorophosphate / 1,2-dichloro-ethane / 24 - 88 °C / Inert atmosphere; Large scale

2.2: 3 h / Inert atmosphere; Large scale

3.1: piperidine / ethanol / 70 h / 79 °C / Inert atmosphere; Large scale

4.1: 5wt.% Rh on activated alumina; triethylamine; hydrogen / tetrahydrofuran / 6 h / 23 - 36 °C / 2585.81 Torr / Inert atmosphere; Autoclave

5.1: acetic acid; sulfuric acid / 50 °C

With piperidine; sulfuric acid; 5wt.% Rh on activated alumina; hydrogen; acetic acid; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; toluene; 2.1: |Vilsmeier-Haack Formylation / 2.2: |Vilsmeier Reaction;
DOI:10.1021/op000286s