Triethylamine → HCID 178489169, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-3-nitro-benzonitrile (2.5 g, 1.4 mmol) in toluene (20 ml) was added sodium azide (1.3 g, 1.8 mmol) and triethylamine hydrochlride (1.5 g, 1.8 mmol), and this mixture stirred at 100° C. fro 48 h. Water was then added (200 ml) and the mixture agitated, the aqueous phase was further washed with water (2×30 ml). The organic phase was then adjusted to pH 2 and the solid which precipitated was filtered off and washed further with water (100 ml) then dried in vacuo (0.05 mmHg, 60° C.) to afford the crude tetrazole. This material was then directly dissolved in MeOH (80 ml), Pd/C (10%) (250 mg) was added and the mixture stirred under 1 atm of hydrogen at 20° C. for ca. 1 h until the theoretical amount of hydrogen (ca. 880 ml) had been taken up. The catalyst was then filtered off and the solvent evaporated to afford the title compound as a white solid (2.2 g, 82% yield), MS: m/e=191.1 (M+). Lit: Synthesis 1998, p910.

Provenance & Evidence