Dimethylformamide → HCID 22914851, compound

HRID 1377486Notes

Reaction equation

HRID 1377486 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:18]([CH3:23])[C:19]2=[O:22])=[CH:14][CH:13]=1>C1CCCCC1>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([CH:3]=[O:4])=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:18]([CH3:23])[C:19]2=[O:22])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 67653590HCID 67653590, compound

Product 1

HCID 22914851HCID 22914851, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

100 ml of dry N,N-dimethylformamide are cooled to 0° C., under an argon atmosphere, 12 ml (128 mmol) of phosphorus oxychloride are added dropwise and the mixture is stirred at room temperature for 1 h. 13.7 g (51 mmol) of 7-chloro-2-methyl-3-phenylisoquinol-1(2 H)-one are added and the mixture is gradually heated to 110° C. and is maintained at this temperature for 4 h. It is cooled to room temperature, the solvent is evaporated under reduced pressure, 200 ml of diethyl ether and ice are added to the residue, 1N sodium hydroxide is added, the organic phase is separated and the aqueous phase is extracted with 200 ml of dichloromethane. The two organic phases are combined, dried over sodium sulphate and filtered and the solvents are evaporated under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of cyclohexane and dichloromethane ranging from 80/20 to 50/50 and then with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30. After recrystallizing from cyclohexane, 7.68 g (26 mmol) of white solid are obtained. Melting point: 172°-173° C.

Workup

  1. temperaturethe mixture is gradually heated to 110° C.
  2. temperatureis maintained at this temperature for 4 h
  3. temperatureIt is cooled to room temperature
  4. customthe solvent is evaporated under reduced pressure, 200 ml of diethyl ether and ice
  5. additionare added to the residue, 1N sodium hydroxide
  6. additionis added
  7. customthe organic phase is separated
  8. extractionthe aqueous phase is extracted with 200 ml of dichloromethane
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. customthe solvents are evaporated under reduced pressure
  12. customThe residue is purified by chromatography on a column of silica gel, elution
  13. additionbeing carried out with a mixture of cyclohexane and dichloromethane ranging from 80/20 to 50/50
  14. additionwith a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30
  15. customare obtained

Sources & evidence

ORD record
ord-f1de1452c80e497db0ae4cfe113a5113
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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