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

HRID 1527104Notes

Reaction equation

HRID 1527104 reaction equation
[CH3:1][C:2](=O)[CH2:3][C:4](=O)[CH3:5].[C:8]([CH2:10][C:11]([NH2:13])=[O:12])#[N:9].C([O-])([O-])=O.[K+].[K+]>O>[CH3:5][C:4]1[CH:3]=[C:2]([CH3:1])[NH:13][C:11](=[O:12])[C:10]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridineYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of pentane-2,4-dione (100 g, 1.0 mol) in H2O (2 L) were added 2-cyanoacetamide (84 g, 1.0 mol) and K2CO3 (13.8 g, 0.1 mol). Then the mixture was stirred at room temperature for 16 hr. The reaction solution was filtrated to give crude product. The crude was washed with water and concentrated to give 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (138 g, 93%).

Workup

  1. filtrationThe reaction solution was filtrated
  2. customto give crude product
  3. washThe crude was washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa76f2d26b634c19a4d5e34cc72a51a1
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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