Triethylamine → HCID 13320449, compound

HRID 544223Notes

Reaction equation

HRID 544223 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](N(CC)CC)[CH3:25]>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]([CH2:24][CH3:25])[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

4

Reactant 2

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

Product 1

HCID 13320449HCID 13320449, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 1-ethyl-6-chloro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 1.7 g (0.005 mole), iodoethyl 1.6 g (0.01 mole), triethylamine 1.0 g (0.01 mole) and dimethylformamide (hereinafter DMF) 20 ml was heated at 90°-100° C. for 7 hours under stirring. After cooling, the reaction mixture was evaporated under vacuum. The residue was dissolved in CHCl3, 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 0.4 g (22%) of 1-ethyl-6-chloro-7-(4-ethyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless needles.

Workup

  1. temperaturewas heated at 90°-100° C. for 7 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. dissolutionThe residue was dissolved in CHCl3
  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-a08643116d594be3b2843663d0c98f49
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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