Tert-butyl (2-fluoro-5-nitrophenyl)carbamate → tert-Butyl (5-amino-2-fluorophenyl)carbamate

HRID 56124Notes

Reaction equation

HRID 56124 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 1

HCID 10988877Tert-butyl (2-fluoro-5-nitrophenyl)carbamate

Product 1

HCID 10933172tert-Butyl (5-amino-2-fluorophenyl)carbamateYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2-fluoro-5-nitrophenyl)carbamate (3.54 g, 13.8 mmol) in MeOH (100 mL) was added catalyst 10% Pd/C (0.15 g). The reaction was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a yellowish solid (2.02 g, 65%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-cfebadd667e648f9a9b6bf132e272e87
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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