3-Methyl-2-nitrobenzoic acid → HCID 178425300, compound

Participants

Reaction Steps

The reaction of 50 g of 3-methyl-2-nitrobenzoic acid and 57.5 g of phosphorus pentachloride in 300 ml of cyclohexane gave, after treatment of the crude product with methylene chloride, 3-methyl-2-nitrobenzoyl chloride melting at about 81°-82° C. A solution of 53.1 g of this acid chloride and 50 ml of tetrahydrofuran was added to a warm solution of 55 g of 5-aminotetrazole monohydrate in 500 ml of tetrahydrofuran and 20 ml of water. The reaction was exothermic, a white precipitate formed and the mixture was allowed to stand for 4 hours. It was then diluted with water, the white precipitate was separated by filtration, washed with water and air dried to give 3-methyl-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 262°-263° C., with decomposition, after recrystallization from a mixture of dimethylformamide and water.

Provenance & Evidence