2-Chloro-4-fluoro-5-nitrophenyl methyl carbonate → 3-Amino-4-fluorophenyl methyl carbonate hydrochloride

HRID 1663634Notes

Reaction equation

HRID 1663634 reaction equation
[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([F:12])=[CH:5][C:4]=1[Cl:13]>CO.[OH-].[OH-].[Pd+2]>[ClH:13].[C:1](=[O:16])([O:14][CH3:15])[O:2][C:3]1[CH:4]=[CH:5][C:6]([F:12])=[C:7]([NH2:9])[CH:8]=1

Participants

4

Reactant 1

HCID 37866902-Chloro-4-fluoro-5-nitrophenyl methyl carbonate

Product 1

HCID 574410313-Amino-4-fluorophenyl methyl carbonate hydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution (20 mL) of 2-chloro-4-fluoro-5-nitrophenyl methyl carbonate (1.00 g, 4.0 mmol) in methanol was added 20% palladium hydroxide on carbon (0.4 g) under a nitrogen atmosphere. The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 5 days. After nitrogen replacement, the catalyst was filtered off. The solvent was evaporated from the filtrate under reduced pressure, and the residue was recrystallized from diethyl ether to give the title compound (759 mg, 86%) as a pale-green powder.

Workup

  1. filtrationAfter nitrogen replacement, the catalyst was filtered off
  2. customThe solvent was evaporated from the filtrate under reduced pressure
  3. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-20847f000db0474187c16360d2d22353
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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