N-methyl-2-pyrrolidone → 7-chloro-3-phenyl-1H-quinolin-2-one

HRID 1075191Notes

Reaction equation

HRID 1075191 reaction equation
Cl[C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:11]([C:18]1[O:19]CC(C)(C)[N:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)[O-].[Na+].CN1CCCC1=O>O.C1(C)C(C)=CC=CC=1>[Cl:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:19])[NH:22]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 134042,4-DichlorobenzaldehydeHCID 98710Oxazole, 4,5-dihydro-4,4-dimethyl-2-(phenylmethyl)-HCID 516919Sodium Bisulfate

Product 1

HCID 122780387-chloro-3-phenyl-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

17.5 g of 2,4-dichlorobenzaldehyde, 18.9 g of 2-benzyl-4,4-dimethyl-2-oxazoline, 1 g of sodium bisulphate, 50 ml of 1-methylpyrrolidin-2-one and 30 ml of xylene are heated at a bath temperature of 170° C., using a water separator, until 2 ml of water have been separated off. 20 ml of solvent are then distilled off at a bath temperature of 220° C., the mixture is stirred under reflux at this temperature for a further 15 minutes and, after cooling, 300 ml of water are added. The precipitate which has separated out is filtered off and washed with water and methanol. Yield: 21.26 g of m. 254°-258° C.

Workup

  1. customuntil 2 ml of water have been separated off
  2. distillation20 ml of solvent are then distilled off at a bath temperature of 220° C.
  3. temperatureunder reflux at this temperature for a further 15 minutes
  4. temperatureafter cooling
  5. addition300 ml of water are added
  6. customThe precipitate which has separated out
  7. filtrationis filtered off
  8. washwashed with water and methanol
  9. custom254°-258° C.

Sources & evidence

ORD record
ord-6fe2241dfaca4331b7dea6c99e480bce
Source dataset
uspto-grants-1983_07
Patent number
US04395414

Reaction notes

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