Ammonia → 2,3-Difluoro-6-nitroaniline

Participants

Reaction Conditions

Reaction Steps

1,2,3-Trifluoronitrobenzene (20.2 g, 114.1 mmol, Aldrich, Milwaukee) and methanolic ammonia (150 mL of a 2.0 molar solution, Aldrich, Milwaukee) were placed in a sealed tube and were heated to 70° C. for 2 h, after which time the solvents were removed in vacuo. The remaining residue was dissolved in ethyl acetate and was extracted with water, saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and the solvents were removed in vacuo to leave a yellow solid. The title compound was recrystallized from water-methanol to afford yellow needles (16.6 g, 84%); 1H NMR (DMSO-d6) δ: 7.94 (m, 1H, Ar—H), 7.56 (br s, 2H, NH2), 6.72 (m, 1H, Ar—H).

Provenance & Evidence