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

HRID 1469150Notes

Reaction equation

HRID 1469150 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-84636181234642f891794a0e227ad139
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

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