Triethylamine → 5-(2-Methylmorpholino)-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-nitroaniline (200 mg, 1.159 mmol) was added to a solution of 2-methylmorpholine (176 mg, 1.738 mmol) in NMP (5 mL) in the presence of triethylamine (0.404 mL, 2.90 mmol). The reaction mixture was heated via microwave irradiation to 100° C. for 1 h. and upon cooling, the solvent was removed by vacuum. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound as a solid in a 70% yield. 1H NMR: (400 MHz, DMSO-d6): δ 7.79 (d, 1H, J=9.6 Hz), 7.25 (bs, 2H), 6.39 (dd, 1H, J=2.8 and 9.6 Hz), 6.20 (d, 1H, J=2.8 Hz), 3.88 (dd, 1H, J=2.8 and 12.0 Hz), 3.69 (d, 1H, J=12.8 Hz), 3.56 (m, 2H), 2.82 (m, 1H), 2.15 (t, 1H, J=7.6 Hz), 1.88 (m, 1H), 1.12 (d, 3H, J=6.0 Hz).

Provenance & Evidence