Ethyl orthoformate → methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

Participants

Reaction Steps

Sodium azide (0.54 g) was added to a stirred solution of 2-methoxy-5-amino benzoic acid, methyl ester (1 g ) and triethyl orthoformate (1.38 ml) in glacial acetic acid (8 ml) and dimethylformamide (2 ml). The mixture was heated to 79°-80°. After 11/4 h the solution was allowed to cool (ice-water bath) and a solution of sodium nitrite (0.57 g) in water (10 ml) was added slowly. After stirring for 30 min, water (40 ml) was added. After 2 h, the mixture was filtered. The residual white solid was washed with water and dried in vacuo, at 25° to give the title compound (0.83 g); mp 185°-187°.

Provenance & Evidence