Pyridine → HCID 10566097, compound

HRID 1461813Notes

Reaction equation

HRID 1461813 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>ClCCl.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][N:9]2[C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 702762-Methylbenzoyl chlorideHCID 889747-Chloro-2,3-dihydro-4-quinolone

Product 1

HCID 10566097HCID 10566097, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 7-chloro-2,3-dihydro-4(1H)-quinolinone (20.0 g), pyridine (26 g) and dichloromethane (200 ml) was added dropwise 2-methylbenzoyl chloride (26 g) at room temperature with stirring. The mixture was stirred under reflux for 4 hours. The reaction mixture was poured into 500 ml of water, then shaken with additional dichloromethane (1000 ml). The organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each) and once with saturated aqueous NaCl solution, then dried over anhydrous sodium sulfate. Solvent was removed in vacuo and the residue was recrystallized to obtain 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone (yield 28 g) as white crystal.

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder reflux for 4 hours
  3. washThe organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each) and once with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolvent was removed in vacuo
  6. customthe residue was recrystallized

Sources & evidence

ORD record
ord-3ffdded0d9e548188aa60d2bfaee7e11
Source dataset
uspto-grants-1991_12
Patent number
US05077410

Reaction notes

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