Oxygen → 4-(4-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 81015Notes

Reaction equation

HRID 81015 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH:17]=O)=[CH:11][CH:10]=1.[C:19]([CH2:21][C:22]([NH2:24])=[O:23])#[N:20].O=O>CS(C)=O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][NH:24][C:22](=[O:23])[C:21]=2[C:19]#[N:20])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 7898CyanoacetamideHCID 641294p-METHOXYCINNAMALDEHYDEHCID 23665647Potassium tert-butoxide

Product 1

HCID 669269194-(4-Methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of potassium tert-butoxide (5.54 g, 49.3 mmol) in DMSO (20 mL) was added to a mixture of (E)-3-(4-methoxyphenyl)acrylaldehyde (2.0 g, 12.33 mmol) and 2-cyanoacetamide (1.140 g, 13.56 mmol) in DMSO (30 mL) dropwise under an oxygen balloon with a water bath cooling outside. After completion of addition, the mixture was stirred under oxygen for 1 h at room temperature, quenched with water (100 mL) and adjusted to pH 5-6 with careful addition of 1 N HCl. A brown precipitate was formed, collected by filtration, washed with water (2×50 mL), dried under vacuum to give 4-(4-methoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.0 g, 36% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.69 (1H, δ, J=6.60 Hz), 7.62 (2H, δ, J=8.80 Hz), 7.11 (2H, δ, J=8.80 Hz), 639 (1H, δ, J=6.60 Hz), 3.87 (3H, s); MS (ES+) m/z: 227 (M+H); LC retention time: 2.532 min (analytical HPLC Method A).

Workup

  1. temperaturecooling outside
  2. additionAfter completion of addition
  3. customquenched with water (100 mL)
  4. additionadjusted to pH 5-6 with careful addition of 1 N HCl
  5. customA brown precipitate was formed
  6. filtrationcollected by filtration
  7. washwashed with water (2×50 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b1821fdc6fc64fe78000a9fa1973a043
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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