Sodium Nitrite → HCID 178498465, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3,4-diamino-5-nitrobenzoate (D245) (2.5 g, 12 mmol, 1 equiv) in AcOH (10 ml) at room temperature was added NaNO2 (900 mg, 13 mmol, 1.1 equiv) and the resulting mixture was stirred at 60° C. for 1 h, cooled to room temperature and concentrated in vacuo. the residue was partitioned between AcOEt and a 5% aqueous citric acid solution and the layers were separated. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. Trituration of the residue in Et2O/iso-hexane gave methyl 4-nitro-1H-1,2,3-benzotriazole-6-carboxylate (D246) (2.08 g, 78%) as an orange solid which was used in the next step without further purification. [M+H]+=223.3, RT=2.31 min.

Provenance & Evidence