Formic Acid → HCID 14211280, compound

HRID 377125Notes

Reaction equation

HRID 377125 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH:18]=2)C#N)[CH:5]=[CH:4][CH:3]=1.[CH:19](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:15][C:14]([CH:19]=[O:20])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 193574065-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

Product 1

HCID 14211280HCID 14211280, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 5-[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-d316f452bab342edb824538507be3703
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Reaction notes

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