Ammonium formate → HCID 14303586, compound

HRID 2350969Notes

Reaction equation

HRID 2350969 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:4]1[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:7](=[O:8])[C:2]([CH3:1])=[C:3]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 14303580HCID 14303580, compound

Product 1

HCID 14303586HCID 14303586, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 50 ml of a suspension of 1.8 g (0.0050 mole) of 3-methyl-1-(2-nitrophenyl)-2,6-diphenyl-4(1H)-pyridinone and 0.2 g of 10% Pd-C in methanol, 1.5 g (0.023 mole) of ammonium formate (as a reducing agent) was added. After heating the resultant mixture under reflux for 3 hours under a nitrogen gas stream, solid matter was filtered off from the reaction mixture and the solvent was distilled off. The residue was then extracted with chloroform and the organic layer (the extract) was washed with 50 ml of a 10% aqueous solution of sodium hydroxide. After washing the organic layer with water, it was dried with anhydrous sodium sulfate and the solvent was then distilled off. The crystals thus-obtained were washed with acetone to give 0.9 g of 1-(2-aminophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of not lower than 300° C.

Workup

  1. temperatureunder reflux for 3 hours under a nitrogen gas stream, solid matter
  2. filtrationwas filtered off from the reaction mixture
  3. distillationthe solvent was distilled off
  4. extractionThe residue was then extracted with chloroform
  5. extractionthe organic layer (the extract)
  6. washwas washed with 50 ml of a 10% aqueous solution of sodium hydroxide
  7. washAfter washing the organic layer with water, it
  8. dry with materialwas dried with anhydrous sodium sulfate
  9. distillationthe solvent was then distilled off
  10. customThe crystals thus-obtained
  11. washwere washed with acetone

Sources & evidence

ORD record
ord-0e872bb850fd444e95ec9a9419402fd6
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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