Ammonium formate → Pyridine, 4-[(3-methoxyphenyl)methyl]-

HRID 273731Notes

Reaction equation

HRID 273731 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)=O>[Pd].C(O)(=O)C.C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[CH2:10][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 23499332HCID 23499332, compound

Product 1

HCID 607965Pyridine, 4-[(3-methoxyphenyl)methyl]-Yield 98.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Ammonium formate (25 g) was added to a mixture of 4-(3-methoxybenzoyl)-pyridine (27 g, 127 mmole) and 10% palladium on charcoal (7 g) in acetic acid (250 ml). The mixture was heated at reflux for 0.5 hr. The mixture was cooled and diluted with an equal volume of methylene chloride. The catalyst was removed and the solution concentrated in vacuo. The residue was dissolved in water and basified with sodium hydroxide. The mixture was extracted with ether. The extracts were dried and concentrated in vacuo to give the crude 4-(3-methoxybenzyl)pyridine (25 g, 98.8%) which was used without purification in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 0.5 hr
  3. temperatureThe mixture was cooled
  4. customThe catalyst was removed
  5. concentrationthe solution concentrated in vacuo
  6. dissolutionThe residue was dissolved in water and basified with sodium hydroxide
  7. extractionThe mixture was extracted with ether
  8. customThe extracts were dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba48f41013cf4acda7cdbc4ae5132b5c
Source dataset
uspto-grants-1995_02
Patent number
US05387593

Reaction notes

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