Water → 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1994231Notes

Reaction equation

HRID 1994231 reaction equation
O.[Na].[CH3:3][CH:4]([C:7](=O)[CH3:8])[CH:5]=O.[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].C([O-])(=O)C.[NH2+]1CCCCC1>C(O)(=O)C>[C:10]([C:12]1[C:13](=[O:14])[NH:15][C:7]([CH3:8])=[C:4]([CH3:5])[CH:3]=1)#[N:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7898CyanoacetamideHCID 3014295Piperidinium acetateHCID 87079555CID 87079555

Product 1

HCID 5905325,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
127 °C

Procedure

Water was added to 2-methyl-3-oxobutanal sodium salt (1-013-01) (34.73 g), and to the reaction mixture was added 2-cyanoacetamide (23.91 g) and 1.76 mol/L piperidinium acetate (119.4 mL), and the reaction mixture was stirred under reflux in an oil bath at 127° C. After 21 h, to the reaction mixture was added gradually dropwise acetic acid (42.7 mL) at 65° C. as internal temperature for 15 min. After the stirring was continued until internal temperature became to 24° C., the resulting crystal was filtered, and washed with water to give 3-cyano-5,6-dimethyl-2-pyridone (1-013-02) (27.76 g, 65.9%, m.p. 258-263° C.).

Workup

  1. custombecame to 24° C.
  2. filtrationthe resulting crystal was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-82d821aaeef84fe2ae224856ef136fcb
Source dataset
uspto-grants-2010_01
Patent number
US07652141B2

Reaction notes

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