Formic Acid → 2-(3-Phenoxyphenoxy)-3-formylpyridine

HRID 467043Notes

Reaction equation

HRID 467043 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[C:17]([C:18]#N)=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=[O:24]>[Ni].O>[O:1]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[C:17]([CH:18]=[O:24])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 197718892-(3-Phenoxyphenoxy)-3-cyanopyridine

Product 1

HCID 197718832-(3-Phenoxyphenoxy)-3-formylpyridine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Crude 2-(3-phenoxyphenoxy)-3-cyanopyridine (15 g) was stirred with Raney nickel alloy (15 g, 50:50) in refluxing 75% formic acid (200 ml) for 2 hours. The reaction mixture was diluted with water and then extracted repeatedly with ether. The combined ether extracts were dried, filtered and evaporated to give an orange oil. Filtration through a plug of silica (eluent hexane-ether, 1:1) afforded 2-(3-phenoxyphenoxy)-3-formylpyridine (3.03 g), infrared max. 1685 cm-1.

Workup

  1. extractionextracted repeatedly with ether
  2. dry with materialThe combined ether extracts were dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an orange oil
  6. filtrationFiltration through a plug of silica (eluent hexane-ether, 1:1)

Sources & evidence

ORD record
ord-b1b8247867514d8588a5ae3d44c33d12
Source dataset
uspto-grants-1992_10
Patent number
US05158954

Reaction notes

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