Cyanoacetamide → 3-Cyano-4,6-dimethyl-2-hydroxypyridine

HRID 1527787Notes

Reaction equation

HRID 1527787 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[C:7]([CH2:10][C:11](=O)[CH3:12])(=O)[CH3:8].C([O-])([O-])=O.[K+].[K+]>O>[CH3:12][C:11]1[CH:10]=[C:7]([CH3:8])[NH:6][C:4](=[O:5])[C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridineYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-cyanoacetamide (8.40 g, 100 mmol) and acetylacetone (10.0 g, 100 mmol) in H2O (200 mL) was added K2CO3 (4.00 g, 28.9 mmol). The mixture was stirred at RT for 22 hours. Then the precipitated solid was filtered with Buchner funnel, washed with ice cold H2O, and dried under vacuum pressure to give 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (13.5 g, 91% yield).

Workup

  1. filtrationThen the precipitated solid was filtered with Buchner funnel
  2. washwashed with ice cold H2O
  3. customdried under vacuum pressure

Sources & evidence

ORD record
ord-45ddff262d8445088c3686263ddcb722
Source dataset
uspto-grants-2015_07
Patent number
US09089575B2

Reaction notes

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