Ammonia → (4-Amino-3-nitrophenyl)methanol

Participants

Reaction Steps

(4-chloro-3-nitrophenyl)methanol (7.0 g, 37.32 mmoles), liquid NH3 (100 mL) and methanol (125 mL) were mixed in a sealed reactor. The temperature was set to 160° C., and the pressure became about 600 psi. After 16 hours, the reaction was cooled down. The high pressure was released. All the solvents were removed. The solid residual was purified by silica gel column to give 4.51 g of the above intermediate (72%). MS (DCI) m/e 169 (M+H)+; 1H NMR (300 MHz, CD3OD) □ 8.02 (d, J=1.70 Hz, 1H), 7.36 (dd, J=8.48, 2.03 Hz, 1H), 6.95 (d, J=8.48 Hz, 1H), 4.48 (s, 2H).

Provenance & Evidence