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

HRID 1885493Notes

Reaction equation

HRID 1885493 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

5

Reactant 2

HCID 14745732benzyl N-(2-hydroxy-4-nitrophenyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 147457335-Amino-2-(benzyloxycarbonylamino)phenol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

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.

Workup

  1. filtrationthe reaction medium is filtered while hot in order
  2. customto remove the catalyst
  3. temperatureOn cooling the filtrate
  4. customthe expected product crystallizes
  5. customdrying
  6. customthe product obtained
  7. customis recrystallized in 96° strength ethanol

Sources & evidence

ORD record
ord-f470ef3bc6324a3f891ce7bc2cfc7601
Source dataset
uspto-grants-1992_09
Patent number
US05145483

Reaction notes

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