Hydrochloric Acid → 4-(Benzyloxy)benzene-1,2-diamine

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

To a solution of 4-benzyloxy-2-nitroaniline (2.31 g, 9.46 mmol) in acetic acid (50 ml) was added conc. hydrochloric acid (1 ml), and gradually added zinc powder (2.16 g, 0.330 mmol) with ice-cooling and the mixture was stirred for 15 minutes, and further added gradually zinc powder (2.16 g, 0.33 mmol) and stirred for 20 minutes. The reaction solution was filtered with celite, and the filtrate was concentrated in vacuo. The resulting residue was dissolved in chloroform and neutralized with a saturated sodium bicarbonate solution. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo to provide 2.01 g (yield 99%) of crude 4-benzyloxy-1,2-phenylenediamine.