Tert-butyl (3-methoxy-2-nitrophenyl)carbamate → N-tert-Butyloxycarbonyl-3-methoxy-2-amino Aniline

HRID 1182484Notes

Reaction equation

HRID 1182484 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[N+:17]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni].O.[H][H]>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[NH2:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 1

HCID 10587951Tert-butyl (3-methoxy-2-nitrophenyl)carbamate

Product 1

HCID 10799950N-tert-Butyloxycarbonyl-3-methoxy-2-amino AnilineYield 55%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of the N-tert-Butyloxycarbonyl-3-methoxy-2-nitro aniline (4 mmol) in MeOH was added catalytic amount of Raney Nickel in water, hydrogen was applied at 40 psi and the mixture was stirred overnight. The mixture was filtered over Celite and the solvent was evaporated to give the desired product in 55% yield. MS (ESI)=239 (MH+).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7b7fa9d0503d4a919c5167dd4a865465
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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