Cyanoacetamide → 1,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

HRID 1995631

Reaction equation

HRID 1995631 reaction equation
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].C[O-].[Na+].C(OCC)(=O)C>CO.O>[C:15]([C:17]1[C:18](=[O:19])[NH:20][C:5]([CH3:6])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1)#[N:16]

Participants

7

Reactant 4

HCID 7898CyanoacetamideHCID 8857Ethyl AcetateHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 10942334Sodium Methoxide

Product 1

HCID 202311,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 4-dimethylamino-3-phenyl-3-butene-2-one (14.1 grams) and cyanoacetamide (5.9 grams) in 100 ml methanol was added to sodium methoxide (7.9 grams) in 100 ml methanol. The mixture was refluxed for 18 hours and then the crude reaction was stripped and the residue dissolved in a small amount of hot water. Acidification to pH 6-7 gave a gum-like solid which was collected by filtration. Further acidification to a lower pH gave only an oil. Trituration of the gum with ethyl acetate and chilling resulted in an off-white solid which was identified by NMR as the desired product, yield 2.8 grams, m.p. 280°-290° C.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customthe crude reaction
  3. customAcidification to pH 6-7 gave a gum-like solid which
  4. filtrationwas collected by filtration
  5. customFurther acidification to a lower pH gave only an oil
  6. customresulted in an off-white solid which

Sources & evidence

ORD record
ord-ac9ef9b7538d471e8226a7b9c029c0e4
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Linked notes

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