Methylamine → 2-fluoro-3-methoxy-N-methyl-6-nitroaniline

Participants

Reaction Steps

A solution of 2,3-Difluoro-4-nitroanisole (7-1, 1.0 g, 5.29 mmol) in EtOH (20 ml) was treated with Methylamine (2M in THF, 3.17 ml, 6.35 mmol, 1.2 eq) and the resulting yellow solution was stirred at 23 deg C. for 1 h. The reaction was complete by LC/MS, but allowed to stir at 23 deg C. for an additional 17 h. The residual bright orange-yellow solution was concentrated in vacuo, then partitioned between EtOAc (2×80 ml) and water (90 ml). The combined organic layers were dried over Na2SO4 and concentrated, leaving the title compound, 2-fluoro-3-methoxy-N-methyl-6-nitroaniline (7-2), as an orange solid with >90% purity. 1H NMR (500 MHz, CDCl3) δ 8.01 (d, 1H, J=1.9 Hz), 7.84 (bs, 1H), 6.81-6.83 (m, 1H), 3.95 (s, 3H), 3.24 (m, 3H). LRMS m/z: Calc'd for C8H9FN2O3 (M+H) 201.2, found 200.9.

Provenance & Evidence