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

HRID 1869271Notes

Reaction equation

HRID 1869271 reaction equation
[H-].[Na+].CN(C)[CH:5]=[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=O.[C:23]([CH2:25][C:26]([NH2:28])=[O:27])#[N:24].Cl>CN(C=O)C.CO>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[NH:28][C:26](=[O:27])[C:25]([C:23]#[N:24])=[CH:5][C:6]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 672186983-(Dimethylamino)-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 (1-2; 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 (1-3). 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-a270681eef57424bb2ef9a9256f19d4b
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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