27798-76-1

Basic information

• Product Name: 1H-Indole-2-propionic acid methyl ester
• Synonyms: 1H-Indole-2-propionic acid methyl ester
• CAS NO: 27798-76-1
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 27798-76-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-2-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-propionic acid methyl ester(27798-76-1)
• EPA Substance Registry System: 1H-Indole-2-propionic acid methyl ester(27798-76-1)

Safety Data

• Hazardous Substances Data: 27798-76-1(Hazardous Substances Data)

Upstream product

• 81784-69-2 N-Hydroxy-3-oxo-4,N-diphenyl-butyramide 
• 66696-85-3 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxy-butyric acid methyl ester 
• 81803-80-7 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-4-oxo-butyric acid methyl ester 
• 81784-66-9 5-(Hydroxy-phenyl-carbamoyl)-4-oxo-pentanoic acid methyl ester 

Relevant articles and documents

New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines

Convenient and regiospecific synthesis of 2-substituted indol (3) by thermolysis of N-acylacetylphenylhydroxylamine (1) and its mechanism including the formation of a radical intermediate are reported.

Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement

Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization