Potassium Carbonate → 6-(Hydroxymethyl)-3-methylpyridine-2-carbonitrile

HRID 2356633Notes

Reaction equation

HRID 2356633 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]#[N:20])[N:13]=1)(=O)C>CO>[OH:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]#[N:20])[C:15]([CH3:18])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68457380(6-Cyano-5-methyl-2-pyridinyl)methyl acetate

Product 1

HCID 573366546-(Hydroxymethyl)-3-methylpyridine-2-carbonitrileYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (82 mg) was added to a solution of (6-cyano-5-methyl-2-pyridinyl)methyl acetate (3.62 g) in methanol (25 ml) and the mixture stirred under argon at ambient temperature for 2 hours. It was concentrated in vacuo to ca. ¼ volume and water (50 ml) added. The mixture was neutralized with 5% acetic acid (1.5 ml) and extracted with dichloromethane (50 ml then 2×25 ml). The combined extracts were washed with brine (25 ml), dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from ether:hexane to afford the title compound (2.26 g, 80%) as a pale buff solid.

Workup

  1. concentrationIt was concentrated in vacuo to ca. ¼ volume and water (50 ml)
  2. additionadded
  3. extractionextracted with dichloromethane (50 ml
  4. washThe combined extracts were washed with brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallised from ether

Sources & evidence

ORD record
ord-7c9d407ef1f14dfd88a1061dbfac36d0
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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