Ammonium formate → HCID 59163377, compound

HRID 889494Notes

Reaction equation

HRID 889494 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH2:8][C:7]1[C:6]([F:11])=[CH:5][C:4]([CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59163388HCID 59163388, compound

Product 1

HCID 59163377HCID 59163377, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Diethyl (3,5-difluoro-4-nitrophenyl)propanedioate (2.08 g, 6.56 mmol) was added to ethanol (100 ml). 10% Palladium on carbon (wet paste) (0.208 g) was then added under a flow of argon. This was treated with ammonium formate (2.07 g, 32.80 mmol) and the reaction heated to reflux for 30 minutes. Once cooled to room temperature the mixture was filtered through celite and washed with ethanol. This was evaporated to a brown oily solid. Triturating in DCM removed insoluble impurities. The liquors were evaporated and then purified by chromatography eluting with 5-40% ethyl acetate in hexane. The clean fractions were evaporated to give the title compound as a pale brown oil (0.774 g, 2.70 mmol). LC/MS: Rt=2.69, [MH]+ 288.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 30 minutes
  3. filtrationwas filtered through celite
  4. washwashed with ethanol
  5. customThis was evaporated to a brown oily solid
  6. customTriturating in DCM removed insoluble impurities
  7. customThe liquors were evaporated
  8. custompurified by chromatography
  9. washeluting with 5-40% ethyl acetate in hexane
  10. customThe clean fractions were evaporated

Sources & evidence

ORD record
ord-c80440d75f9a43279b685c776b01ba57
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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