Ammonium Chloride → Methyl 2-amino-3-methyl-5-nitrobenzoate

Participants

Reaction Steps

To a suspension of 8-methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione ((Example 295: step b) 1.04 g, 4.68 mmol) in methanol (30 mL) was added a solution of sodium methoxide (0.5 M, 0.94 mL, 4.7 mmol) in methanol. The mixture was stirred at ambient temperature for 1 hour and neutralized by addition of saturated NH4Cl. Methanol was removed under reduced pressure and the resulting mixture was filtered. The solids were washed with H2O (twice), dried in high vacuum to give the product (0.97 g, 99% yield) as a yellow solid. 1H NMR (DMSO) δ 8.48 (d, 1H, J=2.7 Hz), 8.02–8.01 (m, 1H), 7.75 (br s, 2H), 3.86 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence