Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

HRID 328570Notes

Reaction equation

HRID 328570 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH2:31][CH2:32][Cl:33])(C1C=CC(C)=CC=1)(=O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH2:31][CH2:32][Cl:33])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydrideHCID 345422Ethyl 7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 13174336Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

Conditions

Temperature
100 °C

Procedure

To a mixture containing 23.4 g of ethyl 7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate and 6.9 g of 65% sodium hydride was added 90g of 2-tosyloxyethyl chloride. The resulting mixture was heated at 100° C for 4 hours. After concentration to dryness, the residue was extracted with chloroform. The extract was washed with water, and dried over anhydrous sodium sulfate. The solvent was removed by the distillation to leave a solid which was recrystallized from ethanol to give ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate, m.p. 207.5°-209.5° C.

Workup

  1. concentrationAfter concentration to dryness
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by the distillation
  6. customto leave a solid which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c04490d568ec45cd938521fcc59bae22
Source dataset
uspto-grants-1977_04
Patent number
US04017622

Reaction notes

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