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

HRID 222424Notes

Reaction equation

HRID 222424 reaction equation
C1(C[C:8]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=2[F:26])(C([O-])=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[F:26])[CH3:13]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67087875Ethyl phenylmethyl(2-fluoro-4-nitrophenyl)propanedioate

Product 1

HCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetateYield 60.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl phenylmethyl(2-fluoro-4-nitrophenyl)propanedioate (3.86 g, 10.6 mmol) dissolved in ethanol, was treated with ammonium formate (6.7 g, 10.6 mmol) and palladium on carbon 10% paste (380 mg) was added under argon. The reaction mixture was refluxed for 3 hours, cooled and filtered. Evaporated and purified by chromatography on silica gel eluting with ethyl acetate/hexane (1:1) to give the title compound as a yellow oil (1.26 g). LC/MS: Rt=2.10, [MH]+ 198.

Workup

  1. additionwas added under argon
  2. temperatureThe reaction mixture was refluxed for 3 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customEvaporated
  6. custompurified by chromatography on silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-10ef9c6b891645169024d3398ccc6fa8
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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