Trifluoroacetic acid → HCID 13320450, compound

HRID 544225Notes

Reaction equation

HRID 544225 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].[F:24][C:25]([F:30])([F:29])[C:26](O)=[O:27]>ClCCl>[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]([C:26](=[O:27])[C:25]([F:30])([F:29])[F:24])[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 6422Trifluoroacetic acidHCID 30516953-Quinolinecarboxylic acid, 1,4-dihydro-6-chloro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 13320450HCID 13320450, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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), anhydrous trifluoroacetic acid 4.2 g (0.02 mole) and dichloromethane 4 ml was stirred at room temperature for 3 hours. The reaction mixture was evaporated under vacuum and the residue was recrystallized from a mixed solvent of DMF and ethanol to obtain 1.8 g (86%) of 1-ethyl-6-chloro-7-(4-trifluoroacetyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless plates. Melting point: 297°-298° C. (decomposition).

Workup

  1. customThe reaction mixture was evaporated under vacuum
  2. customthe residue was recrystallized from a mixed solvent of DMF and ethanol

Sources & evidence

ORD record
ord-ddc77e8c42ac4afaa859868bd9fd1b16
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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