Formic Acid → HCID 14211280, compound

HRID 1194080Notes

Reaction equation

HRID 1194080 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.C(O)=[O:20]>[Ni]>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:20])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 142112794-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

Product 1

HCID 14211280HCID 14211280, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 4-[2-(6-methyl-2-pyridyl)ethoxy]benzonitrile (9.62 g), Raney nickel alloy (10.0 g) and 75% formic acid (150 ml) was heated under reflux for 1 hour. The reaction mixture was filtered and the filtrate was concentrated. The residue was diluted with water, alkalinized with 4N-KOH, and extracted with ethyl ether. The ethyl ether layer was washed with water and dried (MgSO4) and the solvent was distilled off. The residue was recrystallized from ethyl etherhexane to give 4-[2-(6-methyl-2-pyridyl)ethoxy]benzaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl ether
  7. washThe ethyl ether layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationthe solvent was distilled off
  10. customThe residue was recrystallized from ethyl etherhexane

Sources & evidence

ORD record
ord-f1ed2c6a6c474a59b403e51c852bb185
Source dataset
uspto-grants-1989_03
Patent number
US04812570

Reaction notes

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