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

HRID 2391130Notes

Reaction equation

HRID 2391130 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-1c3eb9fe5d53470b9188a090e6eb1dc5
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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