tert-Butyl [(4-fluoro-3-nitrophenyl)methyl]carbamate → tert-Butyl [(3-amino-4-fluorophenyl)methyl]carbamate

HRID 2366748Notes

Reaction equation

HRID 2366748 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[N+:17]([O-])=O>CO.[C].[Pd]>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 53420783tert-Butyl [(4-fluoro-3-nitrophenyl)methyl]carbamate

Product 1

HCID 53439222tert-Butyl [(3-amino-4-fluorophenyl)methyl]carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (4-fluoro-3-nitrophenyl)methylcarbamate (1.0 g, 3.70 mmol) in methanol (4 mL) was added 10% palladium-carbon (150 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere (1 atm) for 18 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (0.88 g, 99%) as a brown oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  4. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fbd03f4d51af4a36990ed0dbf1abd520
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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