benzyl N-(2-hydroxy-4-nitrophenyl)carbamate → 5-Amino-2-(benzyloxycarbonylamino)phenol

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=1[OH:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[C:13]([OH:21])[CH:14]=1

Participants

Procedure

0.53 mole (153 g) of 2-(benzyloxycarbonylamino) -5-nitrophenol in 1 liter of ethanol is subjected to a hydrogen pressure of 8×105 pascals (8 bars) in an autoclave in the presence of 60 g of Raney nickel (water content 50%). After 1 hour at 65° C., the reaction medium is filtered while hot in order to remove the catalyst. On cooling the filtrate, the expected product crystallizes. After draining and drying, the product obtained is recrystallized in 96° strength ethanol. It melts at 148° C.