1H-Indole-4-acetic acid, ethyl ester

Base Information

• Chemical Name: 1H-Indole-4-acetic acid, ethyl ester
• CAS No.: 84401-16-1
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.241
• Mol file: 84401-16-1.mol

Synonyms:

Chemical Property of 1H-Indole-4-acetic acid, ethyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

EthylIndole-4-acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl indole-4-acetate (cas# 84401-16-1) is used as a reactant in the preparation of substituted bisthiadiazoles as glutaminase inhibitors useful in the treatment of cancer.

Technology Process of 1H-Indole-4-acetic acid, ethyl ester

There total 7 articles about 1H-Indole-4-acetic acid, ethyl ester 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: 80.0%

4-(ethoxycarbonylethylidene)-4,5,6,7-tetrahydroindole (107170-60-5) → 4-(carboethoxymethyl)indole (84401-16-1)

Guidance literature:

palladium on activated charcoal; In various solvent(s); at 200 ℃; for 3h;

DOI:10.3987/R-1986-09-2611

Reference yield:

1H-indole-4-carboxylic acid (2124-55-2) → 4-(carboethoxymethyl)indole (84401-16-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / dimethylformamide / 3 h / 65 - 70 °C

2: 97 percent / sodium hydroxide / tetra-n-butylammonium hydrogen sulfate / CH₂Cl₂ / 0.5 h / 15 °C

3: 93 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 12 h / 1551.4 Torr / Ambient temperature

4: thionyl chloride / CH₂Cl₂ / 12 h / Heating

5: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C

6: 0.084 g / silver benzoate, triethylamine / 1 h / Heating

With sodium hydroxide; thionyl chloride; hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

benzyl indole-4-carboxylate (84401-11-6) → 4-(carboethoxymethyl)indole (84401-16-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / sodium hydroxide / tetra-n-butylammonium hydrogen sulfate / CH₂Cl₂ / 0.5 h / 15 °C

2: 93 percent / hydrogen / 10percent palladium on charcoal / ethyl acetate / 12 h / 1551.4 Torr / Ambient temperature

3: thionyl chloride / CH₂Cl₂ / 12 h / Heating

4: triethylamine / tetrahydrofuran; diethyl ether / 3 h / 0 °C

5: 0.084 g / silver benzoate, triethylamine / 1 h / Heating

With sodium hydroxide; thionyl chloride; hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

upstream raw materials:

ethanol

1-benzoyl-4-diazoacetylindole

4-(ethoxycarbonylethylidene)-4,5,6,7-tetrahydroindole

1H-indole-4-carboxylic acid