Ethyl chloroacetate → HCID 13320451, compound

HRID 544226Notes

Reaction equation

HRID 544226 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:19])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2].[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Cl)[CH3:25].C(N(CC)CC)C>CN(C=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:19])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:30])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 30516953-Quinolinecarboxylic acid, 1,4-dihydro-6-chloro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 13320451HCID 13320451, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6-chloro-7-(1-piperazinyl)-4-oxo-1,4-dihydoquinoline-3-carboxylic acid 1.7 g (0.01 mole), ethylchloroacetate 1.2 g (0.01 mole), triethylamine 1.0 g (0.01 mole) and DMF 10 ml was heated at 90°-100° C. for 3 hours under stirring. The reaction mixture was cooled, evaporated under vacuum, the residue was dissolved in dichloromethane, washed with water, dried with anhydrous Na2SO4, and the solvent was distilled off. The residue was recrystallized from a mixed solvent of DMF and ethanol to obtain 2.1 g (quantitative) of 1-ethyl-6-chloro-7-(4-ethoxycarbonylmethyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless powders.

Workup

  1. temperaturewas heated at 90°-100° C. for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried with anhydrous Na2SO4
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from a mixed solvent of DMF and ethanol

Sources & evidence

ORD record
ord-455234286f324be5a53f3c470a67e052
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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