5-METHYL-4-NITRO-1H-1,2,3-BENZOTRIAZOLE synthesis

Yield:31995-60-5 94%

Reaction Conditions:

with nitric acid in conc. sulphuric acid;

Steps:

iii 4-Nitro-5-methyl-1H-benzotriazole [23]

4-Nitro-5-methyl-1H-benzotriazole [23] Nitric acid (40ml, excess) was added drop wise over 20 minutes to a stirred solution of 5-methyl-1H-benzotriazole (2.66g, 20mmol) in conc. sulphuric acid (40ml) at 0°C., Stirring was continued at room temperature for 90 minutes by which time TLC (A) indicated complete reaction. The solution was poured onto ice to precipitate a flocculent white solid. The solid was collected by filtration and washed with water to afford [23] in 94% yield. R_f(A) 0.60 δ_H(400MHz; DMSO-d₆) 2.79 (3H, s, CH₃) 7.52 (1H, d, J8.4, BT) 8.36 (1H, br s, BT) 16.26 (1H, s, NH); m/z (EI-HR) 178.04937 [(M) calc. for C₇H₆N₄O₂ 178.04908].

References:

EP1272827,2008,B1