77069-13-7

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, 3-benzoyl-, ethyl ester
• CAS NO: 77069-13-7
• Molecular Formula: C18H15NO3
• Molecular Weight: 293.322
• Mol File: 77069-13-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, 3-benzoyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, 3-benzoyl-, ethyl ester(77069-13-7)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, 3-benzoyl-, ethyl ester(77069-13-7)

Safety Data

• Hazardous Substances Data: 77069-13-7(Hazardous Substances Data)

Upstream product

• 3770-50-1 2-carbethoxyindole 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 33268-96-1 3-benzoylindole-2-carboxylic acid 
• 24370-88-5 ethyl 3-benzyl-1H-indole-2-carboxylate 
• 324002-16-6 3-benzyl-1-(3-dimethylamino-propyl)-1H-indole-2-carboxylic acid 
• 324002-25-7 ethyl 3-benzyl-1-(3-dimethylaminopropyl)-1H-indole-2-carboxylate 
• 15224-25-6 3-benzoylindole 

Relevant articles and documents

Synthetic Studies on Indoles and Related Compounds. XV. An Unusual Acylation of Ethyl Indole-2-Carboxylate in the Friedel-Crafts Acylation

The Friedel-Crafts reaction of ethyl indole-2-carboxylate (1a) with acyl chlorides or acid anhydrides in the presence of Lewis acids was investigated in order to establish a preparative procedure for the corresponding ethyl 3-acylindole-2-carboxylates (4).Although monoacylation occured successfully, the products were generally a mixture of ethyl 3-, 5-, and 7-acylindole-2-carboxylates (4,5 and 6).The ratio of the yields of these three products varied greatly depending on reaction conditions and reagents used.A tendency that the 3-acylindole (4) was obtained as a main product was observed when a Lewis acid other than aluminum chloride was used as a catalyst and/or an acyl chloride derived from a weaker acid was employed, whereas a tendency for formation of the 5- and 7-acylindoles (5 and 6) was observed when aluminum chloride and/or an acyl chloride derived from a stronger acid was used.As to the 5- and 7-acylindoles (5 and 6) , the yields of the former were always much higher than those of the latter (6).The result indicates that ethyl 3- and 5-acylindole-2-carboxylates can be regioselectively prepared from a common substrate (1a) by changing the reaction conditions or reagents. friedel-craft acylation; ethyl indole-2-carboxylate; acyl chloride; acid anhydride; lewis acid; aluminum chloride; acylindole

THE FRIEDEL-CRAFTS ACYLATION OF ETHYL INDOLE-2-CARBOXYLATE. AN USUAL SUBSTITUTION ON THE BENZENE MOIETY.

Ethyl indole-2-carboxylate can be acylated with a variety of acyl chlorides under Friedel-Crafts conditions to give mono-acyl indole derivatives.However, the acyl chloride derived from a stronger acid tends to substitute at the C-5 position rather than at