Formic Acid → HCID 21846110, compound

HRID 619193Notes

Reaction equation

HRID 619193 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#N)=[CH:3][CH:2]=1.C(O)=[O:18]>[Ni]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:18])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 218460893-(4-Pyridinylmethoxy)benzonitrile

Product 1

HCID 21846110HCID 21846110, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 3-(4-pyridinylmethoxy)benzonitrile (2.5 g, 0.012 mol) in 75% formic acid (35 ml) was treated with raney nickel (2 g) and heated to reflux for 4 hours. The reaction mixture was filtered through SUPERCELL®, the filtrate was brought to a pH of 8-9 with 5N NaOH, extracted with EtOAc (3×150 ml) and the combined organic layers were dried over MgSO4, filtered and stripped. The residue was purified by column chromatography on silica gel eluting with EtOAc (100%) to afford 0.94 g (37%) of 3-(4-pyridinylmethoxy)benzaldehyde.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction mixture was filtered through SUPERCELL®
  4. extractionextracted with EtOAc (3×150 ml)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customThe residue was purified by column chromatography on silica gel eluting with EtOAc (100%)

Sources & evidence

ORD record
ord-ccabac1ac1664bdd84b5bdff264341ef
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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