Benzoyl chloride → 3-Benzoylamino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

HRID 229678Notes

Reaction equation

HRID 229678 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.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.N1C=CC=CC=1>[C:21]([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)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 223191193-Amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Product 1

HCID 223190303-Benzoylamino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-oneYield 83.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

30 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 1 ml of methylene chloride and 1 ml of pyridine, to which 19 mg of benzoyl chloride was added with cooling with ice, and the mixture was stirred at room temperature for a night. The reaction mixture was concentrated, diluted with ethyl acetate, and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried by magnesium sulfate, and refined by NH silica gel chromatography (ethyl acetate). The solvent was concentrated, and the resultant crude crystal was washed with ethyl acetate/hexane, to obtain 35 mg of the subject compound.

Workup

  1. temperaturewith cooling with ice
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried by magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. washthe resultant crude crystal was washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-3772fe50fe344e109b2df56e68d9ae37
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

Loading…