2-Methoxy-3-cyano-5-ethyl-6-methylpyridine → 2-Methoxy-3-(aminomethyl)-5-ethyl-6-methylpyridine

HRID 1033010Notes

Reaction equation

HRID 1033010 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][C:6]([CH2:11][CH3:12])=[C:5]([CH3:13])[N:4]=1>CO.Cl.[Pd]>[CH3:1][O:2][C:3]1[C:8]([CH2:9][NH2:10])=[CH:7][C:6]([CH2:11][CH3:12])=[C:5]([CH3:13])[N:4]=1

Participants

5

Reactant 1

HCID 104422282-Methoxy-3-cyano-5-ethyl-6-methylpyridine

Product 1

HCID 103299382-Methoxy-3-(aminomethyl)-5-ethyl-6-methylpyridineYield 89.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-methoxy-3-cyano-5-ethyl-6-methylpyridine (344 mg, 1.95 mmol) in methanol (8 mL) and 4.9M methanolic HCl (5 mL) containing 5% palladium on carbon (100 mg) was hydrogenated at atmospheric pressure for 10-20 hours. The catalyst was filtered off and the solvent evaporated. This residue was made basic with sodium hydroxide and the product was extracted into methylene chloride, dried (Na2SO4), filtered and evaporated to give 313 mg (89% yield) of oily product.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. extractionthe product was extracted into methylene chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6a900438c31649d6a09702299752c5b5
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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