Formic Acid → 4-(3-Formylphenyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine

HRID 2247868Notes

Reaction equation

HRID 2247868 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]([CH3:21])[C:10]=2[C:22](=[O:32])[NH:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:6]=[CH:7][CH:8]=1)#N.C(O)=[O:34]>[Ni]>[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]([CH3:21])[C:10]=2[C:22](=[O:32])[NH:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH:6]=[CH:7][CH:8]=1)=[O:34]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 198159053-(2-Morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine

Product 1

HCID 198159124-(3-Formylphenyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 4-{3-cyanophenyl)-2-methyl-3-(2- morpholinoethylcarbamoyl)-6-phenylpyridine (1.5 g) and Raney's Nickel (1.5 g) in 75% formic acid (40 ml) was refluxed for one hour under stirring. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and the resultant solution was adjusted to pH 8.0 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to a column chromatography on silica gel and eluted with a mixture of ethyl acetate and diisopropyl ether (8:2 V/V). The eluted solution was evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 4-(3-formylphenyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (0.8 g).

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. washeluted with a mixture of ethyl acetate and diisopropyl ether (8:2 V/V)
  9. customThe eluted solution was evaporated in vacuo
  10. customthe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-ef31e5c36b554d7dadee57cae28918ef
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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