Anthranilic Acid → HCID 178515044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture was prepared from 10 g of 5-aminotetrazole and 50 ml N,N-dimethylformamide. This was heated to 100° C. and 17 g of triethoxymethane was added. The resulting mixture was stirred at 100° C. under nitrogen for 2 hours and then a solution of the ammonium salt of anthranilic acid (prepared from 16 g of anthranilic acid and 7.8 ml of 14.8M ammonium hydroxide in methanol, followed by removal of the methanol) in 40 ml of N,N-dimethylformamide was added. The mixture was stirred for 1 hour at 100° C., then cooled to room temperature and finally cooled in an ice bath to induce crystallization. The white crystals which formed were separated by filtration, washed with N,N-dimethylformamide and then with carbon tetrachloride, and vacuum oven dried to give the ammonium salt of 3-(1H-tetrazol-5-yl)4(3H)-quinazolinone.

Provenance & Evidence