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Morpholine → 1-Ethyl-5,6,8-trifluoro-1,4-dihydro-7-(4-morpholinyl)-4-oxo-3-quinolinecarboxylic acid

HRID 2165668
Notes
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Reaction equation

HRID 2165668 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][O:24][CH2:23][CH2:22]1.CN1CCCC1=O>CCOCC>[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][O: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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8083MorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 148393511-Ethyl-5,6,8-trifluoro-1,4-dihydro-7-(4-morpholinyl)-4-oxo-3-quinolinecarboxylic acidYield 38.5%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 289 mg of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 300 mg of morpholine and 5.6 ml of 1-methyl-2-pyrrolidone was heated in a stoppered flask at 65° C. for one hour. Ether was added, the solid collected, dissolved in 200 ml of acetone, filtered and boiled down to about 50 ml. The solid was collected, giving 137 mg of the desired product, mp 281°-283° C.

Workup

  1. customthe solid collected
  2. dissolutiondissolved in 200 ml of acetone
  3. filtrationfiltered
  4. customThe solid was collected

Sources & evidence

ORD record
ord-9ff21faeb5b64ceaa33099edebbb8554
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04940710

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes