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

HRID 1879108Notes

Reaction equation

HRID 1879108 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 60.3%

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-2ed65196251c41868a0d23cd7bf7b0f3
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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