Triethylamine → 1-Ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 544227Notes

Reaction equation

HRID 544227 reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:20])=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:12]=2)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]1)[CH3:3].[OH:25][CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=O)[O:27]1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:20])=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH:28]4[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:26](=[O:25])[O:27]4)[CH2:16][CH2:15]3)[CH:12]=2)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 38042593-Hydroxyisobenzofuran-1(3H)-oneHCID 12733912Defluoro-6-chloro Norfloxacin Hydrochloride

Product 1

HCID 133204541-Ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6-chloro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride 1.9 g (0.005 mole), 3-hydroxyphthalide 0.75 g (0.005 mole), triethylamine 0.5 g (0.005 mole) and DMF 10 ml was heated at 100°-110° C. for 8 hours under stirring. After cooling, the reaction mixture was evaporated under vacuum. The residue was dissolved in dichloromethane, washed with water and dried with anhydrous Na2SO4. After removing the solvent, the residue was recrystallized from a mixed solvent of DMF and ethanol to obtain 1.8 g (78%) of 1-ethyl-6-chloro-7-(4-phthalidyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless powders.

Workup

  1. temperaturewas heated at 100°-110° C. for 8 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried with anhydrous Na2SO4
  7. customAfter removing the solvent
  8. customthe residue was recrystallized from a mixed solvent of DMF and ethanol

Sources & evidence

ORD record
ord-d450b48e86b8497f8a72b0c7f3d12299
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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