Acetic Acid → HCID 69205369, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-1-benzo[1,3]dioxol-5-yl-1-cyano-1H-indene-2-carboxylic acid methyl ester (10 g) and acetic acid, (30 mL) were heated to 100° C.; 60% aqueous sulfuric acid (20 mL) was added with stirring during 30 min. The mixture was heated to 110° C. for 6 h, cooled to rt, extracted with toluene (50+10 mL), washed with water (3×100 mL), extracted with 0.1 M aqueous sodium hydroxide (100+20 mL), acidified with concentrated hydrochloric acid, extracted with toluene (25+10 mL), and filtrated through activated carbon. Removal of the toluene gave 80% of 1-(benzo[1,3]dioxol-5-yl)-3-oxo-indan-1-carboxylic acid. The acid was subsequently decarboxylated by heating to 100° C. in N-methylpyrrolidone (15 mL) for 1 h. After cooling, the solution was poured into water (40 mL) with efficient stirring. Filtration, washing with water (5×20 mL), dissolution in ethyl acetate (40 mL), filtration through activated carbon and removal of the ethyl acetate gave 80% of 3-(benzo[1,3]dioxol-5-yl)-indan-1-one.

Provenance & Evidence