Diethyl Ether → 1-Ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid

HRID 248514Notes

Reaction equation

HRID 248514 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1.CCOCC>CN1CCCC1=O>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 67164ThiomorpholineHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 148393521-Ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 289 mg portion of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was dissolved in 3 ml of 1-methyl-2-pyrrolidone. A 350 mg portion of thiomorpholine was added and the mixture was stirred for 2 hours. Ether was added, the solid collected and recrystallized from acetone, giving 250 mg of the desired product as a white solid, mp 308°-310° C.

Workup

  1. customthe solid collected
  2. customrecrystallized from acetone

Sources & evidence

ORD record
ord-ffdbf1b6a3e0480dbf07d1816839b982
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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