Ammonium formate → HCID 22343598, compound

HRID 583812Notes

Reaction equation

HRID 583812 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][C:11](=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:10]2=[O:28])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:21]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)[C:10]2=[O:28])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54327232HCID 54327232, compound

Product 1

HCID 22343598HCID 22343598, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(3,4-difluorophenyl)-3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one (125 mg, 0.326 mmol), ammonium formate (411 mg, 6.53 mmol) and 10% palladium on carbon (40 mg) in 30 mL of anhydrous methanol was refluxed under nitrogen for 18 hours. After cooling, the catalyst was removed In vacuo and the residue was treated with saturated aqueous sodium bicarbonate and methylene chloride. The organic layer was removed, combined with a second extraction of the aqueous layer with additional methylene chloride, washed with saturated aqueous sodium chloride (NaCl) and dried. The solvent was again removed In vacuo to give the crude product as a white solid (111 mg). This solid was dissolved in hot ethyl acetate and crystallized by the addition of a few drops of hexanes. The title product, 29 mg, has m.p. 130-131° C. From the filtrate a second crop of product was also obtained as above, 50 mg, mp. 130-131° C.

Workup

  1. temperaturewas refluxed under nitrogen for 18 hours
  2. temperatureAfter cooling
  3. customthe catalyst was removed In vacuo
  4. additionthe residue was treated with saturated aqueous sodium bicarbonate and methylene chloride
  5. customThe organic layer was removed
  6. extractioncombined with a second extraction of the aqueous layer with additional methylene chloride
  7. washwashed with saturated aqueous sodium chloride (NaCl)
  8. customdried
  9. customThe solvent was again removed In vacuo

Sources & evidence

ORD record
ord-85906fcb9e4b4d64a3991a7b4765fa7b
Source dataset
uspto-grants-2005_08
Patent number
US06924289B2

Reaction notes

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