Pyridine → HCID 23054596, compound

HRID 1073064Notes

Reaction equation

HRID 1073064 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[S:21][CH:22]=[CH:23][C:24]=1[C:25](Cl)=[O:26]>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:25]([C:24]2[CH:23]=[CH:22][S:21][C:20]=2[CH3:19])=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 889747-Chloro-2,3-dihydro-4-quinoloneHCID 22414448HCID 22414448, compound

Product 1

HCID 23054596HCID 23054596, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 7-chloro-2,3-dihydro-4(lH)-quinolinone (20.0 g), pyridine (26 g) and dichloromethane (200 ml) was added dropwise 2-methyl-3-thienylcarbonyl 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 7-chloro-2,3-dihydro-l-(2-methyl-3-thienylcarbonyl)-4(lH)-quinolinone (yield 28 g) was obtained as colorless oil.

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

Sources & evidence

ORD record
ord-7c3fa7a32f314888a1740e943cb33069
Source dataset
uspto-grants-1990_11
Patent number
US04968680

Reaction notes

Loading…