Hydrochloric Acid → 6-(4-Methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile

HRID 2105512Notes

Reaction equation

HRID 2105512 reaction equation
[H-].[Na+].C(N(CC)[CH:6]=[C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=O)C.[C:25]([CH2:27][C:28]([NH2:30])=[O:29])#[N:26].Cl>CN(C=O)C.CO>[CH3:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[NH:30][C:28](=[O:29])[C:27]([C:25]#[N:26])=[CH:6][C:7]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 690658243-(Diethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one

Product 1

HCID 211032106-(4-Methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a slurry of NaH (1.38 g, 60% in mineral oil, 34.41 mmol) in DMF (20 mL) at 0° C. was added a solution of 3-dimethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one (2-2; 4.15 g, 15.64 mmol) and 2-cyanoacetamide (1.45 g, 17.2 mmol) in MeOH (1.5 mL) and DMF (40 mL) dropwise over 40 min. The resulting mixture was stirred at 90° C. for 4 h and cooled to rt. The mixture was poured into dilute HCl aqueous solution (240 mL, 0.25 M) and filtered, washed with water (40 mL) and dried in vacuo to afford 6-(4-methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile (2-3). 1H-NMR (500 MHz, CDCl3) δ 7.96 (s, 1H), 7.15-7.28 (m, 7H), 7.05-7.07 (m, 2H), 2.36 (s, 3H). LRMS m/z (M+H) Calcd: 287.3, found: 287.1.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. washwashed with water (40 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c3d8c0cfce404c2e99e79bf37cc4f080
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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