Toluene → 3-Benzylamino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

HRID 229679Notes

Reaction equation

HRID 229679 reaction equation
[NH2:1][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[H-].[Na+].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(Cl)C1C=CC=CC=1>C(OCC)(=O)C>[CH2:29]([NH:1][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 223191193-Amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Product 1

HCID 223192493-Benzylamino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

40 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one and 10 mg of sodium hydride were added to 1 ml of toluene, to which 30 mg of benzyl chloride was added dropwise at 70° C. The mixture was stirred for 30 minutes, and heated for 1 hour under reflux. The reaction mixture was left to cool to room temperature, diluted with ethyl acetate, and washed with a water and a saturated saline water. The organic layer was dried by magnesium sulfate, and refined by NH silica gel chromatography (ethyl acetate/hexane-based solvent), to obtain 13 mg of the subject compound.

Workup

  1. additionwas added dropwise at 70° C
  2. temperatureheated for 1 hour
  3. temperatureunder reflux
  4. waitThe reaction mixture was left
  5. washwashed with a water
  6. dry with materialThe organic layer was dried by magnesium sulfate

Sources & evidence

ORD record
ord-db5c41eb99ac4fcf8feb31d8a3a2b9fd
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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