Methyl 2-(2,6-difluoro-4-nitrophenyl)-2-methylpropanoate → Methyl 2-(4-amino-2,6-difluorophenyl)-2-methylpropanoate

HRID 2202314Notes

Reaction equation

HRID 2202314 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14]>CO.[C].[Pd]>[NH2:8][C:6]1[CH:5]=[C:4]([F:11])[C:3]([C:12]([CH3:17])([CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 118622713Methyl 2-(2,6-difluoro-4-nitrophenyl)-2-methylpropanoate

Product 1

HCID 118622743Methyl 2-(4-amino-2,6-difluorophenyl)-2-methylpropanoateYield 101.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(2,6-difluoro-4-nitrophenyl)-2-methylpropanoate (3.2 g, 12.35 mmol) and 10% palladium-carbon (1.314 g, 0.617 mmol, 50%, wet) in MeOH (30 mL) was stirred overnight at room temperature under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane) to give methyl 2-(4-amino-2,6-difluorophenyl)-2-methylpropanoate (2.87 g, 12.52 mmol, 101%) as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c350d56e79454151b555900a8fca0eca
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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