Formic Acid → N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)propionamide

HRID 735185Notes

Reaction equation

HRID 735185 reaction equation
C(O)=[O:2].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:29])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#N)=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>[Ni].O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:29])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([CH:27]=[O:2])=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 68816280N-(4'-chlorobiphenyl-4-yl)-3-(4-cyanophenyl)propionamide

Product 1

HCID 86060754N-(4'-chlorobiphenyl-4-yl)-3-(4-formylphenyl)propionamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

100 mL of formic acid is added to a reaction mixture of 3 g of Raney nickel moistened with water and 14.22 g (39.41 mmol) of N-(4′-chlorobiphenyl-4-yl)-3-(4-cyanophenyl)propionamide and refluxed for 20 hours. Then the catalyst is suction filtered and the filtrate is diluted with plenty of water. The precipitated N-(4′-chlorobiphenyl-4-yl)-3-(4-formylphenyl)propionamide is suction filtered and dissolved in ethyl acetate. The organic phase is washed first of all with 2 molar sodium hydroxide solution, then with water and finally with saturated sodium chloride solution, dried over sodium sulfate and activated charcoal, and freed from solvent by rotary evaporation. Yield: 11.7 g (57% of theory); C22H18ClNO2 (M=363.84); calc.: molecular ion peak (M+H)+: 364/66 (Cl); found: molecular ion peak (M+H)+: 364/66 (Cl); Rf value: 0.5 (silica gel, cyclohexane/ethyl acetate (1:1)).

Workup

  1. temperaturerefluxed for 20 hours
  2. filtrationfiltered
  3. additionthe filtrate is diluted with plenty of water
  4. filtrationfiltered
  5. dissolutiondissolved in ethyl acetate
  6. washThe organic phase is washed first of all with 2 molar sodium hydroxide solution
  7. dry with materialwith water and finally with saturated sodium chloride solution, dried over sodium sulfate and activated charcoal
  8. customfreed from solvent by rotary evaporation

Sources & evidence

ORD record
ord-783c8fc52ac14dafa5ae5c953f571d1c
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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