Ammonium formate → HCID 67059966, compound

HRID 238281Notes

Reaction equation

HRID 238281 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH:15]=1)([O-])=O.C([O-])=O.[NH4+]>O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68008288HCID 68008288, compound

Product 1

HCID 67059966HCID 67059966, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

1-[4-(2-Nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]ethanone (0.43 g, 1.8 mmol) was dissolved in a solution of ammonium formate (1.13 g, 18 mmol) in IMS (20 mL) and water (20 mL). Palladium on carbon (10% w/w, 0.2 g) was then added and the mixture heated at reflux for 1 hour. The solution was filtered and then the solvent removed by evaporation under vacuum. The residue was dissolved in ethyl acetate (50 mL) and the resulting solution washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a pale pink oil (0.3 g). LCMS m/z 219.38 [M+H]+. R.T.=2.29 min (Analytical Method 4).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe solution was filtered
  4. customthe solvent removed by evaporation under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  6. washthe resulting solution washed with saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-ed742dd693e74b56850b79ff6a6c8994
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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