Cyanoacetamide → 6-Methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

HRID 2208656Notes

Reaction equation

HRID 2208656 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[F:7][C:8]([F:16])([F:15])[C:9]([CH2:11][C:12](=O)[CH3:13])=O.C([O-])([O-])=O.[K+].[K+]>O>[CH3:13][C:12]1[NH:6][C:4](=[O:5])[C:3]([C:1]#[N:2])=[C:9]([C:8]([F:16])([F:15])[F:7])[CH:11]=1

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 739431,1,1-Trifluoro-2,4-pentanedione

Product 1

HCID 2474406-Methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrileYield 52.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 2-cyanoacetamide (14.0 g, 166 mmol) and trifluoroacetylacetone (20.0 ml, 166 mmol) in H2O (332 ml) was added K2CO3 (6.60 g, 47.9 mmol). The mixture was stirred at 23° C. for 15 h. The precipitated solid was filtered with Buchner funnel, washed with ice cold H2O, and dried with hot air (60° C., 16 h) to give the titled compound (17.6 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.38 (s, 3H), 6.66 (s, 1H).

Workup

  1. filtrationThe precipitated solid was filtered with Buchner funnel
  2. washwashed with ice cold H2O
  3. customdried with hot air (60° C., 16 h)

Sources & evidence

ORD record
ord-a044fbe07d6c44e9973aaa894834b161
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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