Ammonium formate → Ethyl 2-(4-amino-3-fluorophenyl)acetate

HRID 913175Notes

Reaction equation

HRID 913175 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11](C(OCC2C=CC=CC=2)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58012509Ethyl phenylmethyl (3-fluoro-4-nitrophenyl)propanedioate

Product 1

HCID 59760056Ethyl 2-(4-amino-3-fluorophenyl)acetateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl phenylmethyl (3-fluoro-4-nitrophenyl)propanedioate (11.66 g, 32.3 mmol), ammonium formate (10.2 g, 161.5 mmol) and 10% palladium on carbon (wet paste) (1.7 g, 0.8 mmol) was placed under argon and ethanol (300 ml) introduced. The reaction mixture was heated to 60° C. for 3 hours, cooled and filtered through celite under an argon atmosphere. Evaporated and purified by chromatography on silica gel eluting with 2-30% ethyl acetate in hexane to give the title compound as a yellow oil (5.22 g, 26.5 mmol). LC/MS: Rt=2.14, [MH]+ 198.

Workup

  1. temperaturecooled
  2. filtrationfiltered through celite under an argon atmosphere
  3. customEvaporated
  4. custompurified by chromatography on silica gel eluting with 2-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e33d5a0ff3f9430286ef39da55055505
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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