Hydrochloric Acid → 1-(2,4-Difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2396976Notes

Reaction equation

HRID 2396976 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([CH3:22])[C:15]([F:21])=[C:16]([F:20])[C:17]=2[F:19])[C:12](=[O:23])[C:11]([C:24]([O:26]CC)=[O:25])=[CH:10]1.Cl>C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([CH3:22])[C:15]([F:21])=[C:16]([F:20])[C:17]=2[F:19])[C:12](=[O:23])[C:11]([C:24]([OH:26])=[O:25])=[CH:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14651271Ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate

Product 1

HCID 146512701-(2,4-Difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Employing ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylate (4.3 g) and conc. hydrochloric acid: 90% acetic acid (1:4) (80 ml), the procedure of Reference Example 23 is repeated to give 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (2.93 g), as white powder, m.p. 221°-222° C.

Sources & evidence

ORD record
ord-37e94e2990ee438d815580eae3a60f39
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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