Ammonium formate → Ethyl 2-(4-amino-2-fluorophenyl)acetate

HRID 889484Notes

Reaction equation

HRID 889484 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11](C(OCC1C=CC=CC=1)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59760054Ethyl phenylmethyl (2-fluoro-4-nitrophenyl)propanedioate

Product 1

HCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetateYield 60.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl phenylmethyl (2-fluoro-4-nitrophenyl)propanedioate (3.86 g, 10.6 mmol) dissolved in ethanol (50 ml), was treated with ammonium formate (6.7 g, 10.6 mmol) under argon. Palladium on carbon 10% paste (380 mg) was added and the reaction was stirred under reflux for 3 hours (60° C.). The reaction was cooled to room temperature and the catalyst removed by filtration through celite. Solvent was removed to give a brown oil. The crude material was purified by chromatography on silica gel eluting with 0-50% ethyl acetate in hexane (1:1) over 45 minutes. Fractions were evaporated to give the title compound as a yellow oil (1.26 g, 6.4 mmol).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe catalyst removed by filtration through celite
  3. customSolvent was removed
  4. customto give a brown oil
  5. customThe crude material was purified by chromatography on silica gel eluting with 0-50% ethyl acetate in hexane (1:1) over 45 minutes
  6. customFractions were evaporated

Sources & evidence

ORD record
ord-8bee5a0b0d1b4bcdbb685f8b268441ac
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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