Hydrochloric Acid → HCID 86755148, compound

HRID 377607Notes

Reaction equation

HRID 377607 reaction equation
CN(C(C1C=CC=CC=1)C1C=C([C:11]2[C:12]([NH:22][C:23](=[O:25])[CH3:24])=[C:13]([CH:18]=[CH:19][C:20]=2[Cl:21])[C:14](OC)=[O:15])C=CC=1)C.C(O)C.Cl>C1COCC1>[ClH:21].[OH:15][C:14]1[C:13]2[C:12](=[CH:11][CH:20]=[CH:19][CH:18]=2)[NH:22][C:23](=[O:25])[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70266632HCID 70266632, compound

Product 1

HCID 86755148HCID 86755148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.0 g (4.6 mmol) of methyl 3-(dimethylaminophenyl-methyl)phenyl-2-acetamido-4-chlorobenzoate are dissolved in 15 ml of THF. With cooling, 15 ml of a 1 molar solution of THF and KN[Si(CH3)3 ]2 are added dropwise with stirring. The mixture is additionally stirred at room temperature for 1 1/2 hours. The solvent is distilled off and the residue is treated with water. The solution thus obtained is washed with dichloromethane. The aqueous phase is adjusted to an acidic pH using hydrochloric acid and again extracted with dichloromethane. The organic phase separated off is dried. The solvent is distilled off. For further purification of the oil obtained, the product is taken up with ethanol, acidified with ethereal hydrochloric acid, triturated with ether and the product obtained is filtered off with suction. 7-Chloro-3-[dimethylamino-phenylmethyl)phenyl]-1,2-dihydro-4-hydroxyquinolin-2-one hydrochloride, dihydrate, m.p. ~230°, is obtained.

Workup

  1. temperatureWith cooling
  2. stirringThe mixture is additionally stirred at room temperature for 1 1/2 hours
  3. distillationThe solvent is distilled off
  4. additionthe residue is treated with water
  5. customThe solution thus obtained
  6. washis washed with dichloromethane
  7. extractionagain extracted with dichloromethane
  8. customThe organic phase separated off
  9. customis dried
  10. distillationThe solvent is distilled off
  11. customFor further purification of the oil
  12. customobtained
  13. customtriturated with ether
  14. customthe product obtained
  15. filtrationis filtered off with suction

Sources & evidence

ORD record
ord-55d4cb1d3ff84291810f16567815a8e8
Source dataset
uspto-grants-2000_02
Patent number
US06028080

Reaction notes

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