Dimethylamine → N-Nitroaniline

Participants

Reaction Steps

3,4-Difluoronitrobenzene (3 mL, 27.1 mmol) was added to a solution of dimethyl amine (15 mL, 29.8 mmol) and i-Pr2NEt (5.2 ml, 29.8 mmol) in ethyl acetate (20 mL) at 0° C. and the mixture was stirred at room temperature overnight. The yellow solution was concentrated and redissolved in methylene chloride (100 mL) and then washed with water (50 mL). The aqueous layer was basified with KOH pellets and back extracted with methylene chloride (2×50 mL). The combined organic layer after evaporation afforded a yellow solid which was dissolved in 6N HCl (60 mL) at 0° C. and washed with methylene chloride (3×60 mL). The solution was basified with KOH pellets (pH 10) and extracted with methylene chloride (3×100 mL). The combined organic phase was dried (Na2SO4) and concentrated to provide 272 (1.8 g). Data for 272: 1HNMR (300 MHz, CDCl3): δ 7.95 (dd, J=2, 8 Hz, 1H), 7.88 (dd, J=3, 14 Hz, 1H), 6.72 (t,J=9 Hz, 1H), 3.10 (s, 6H).

Provenance & Evidence