Hydrochloric Acid → 7-Morpholino-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2107609Notes

Reaction equation

HRID 2107609 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:22])[C:6]([C:23]([O:25]CC)=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>>[O:18]1[CH2:19][CH2:20][N:15]([C:11]2[C:12]([CH3:14])=[C:13]3[C:8]([C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:21])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15692410Ethyl 1-cyclopropyl-7-morpholino-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 156225107-Morpholino-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 40.3%

Procedure

To ethyl 1-cyclopropyl-7-morpholino-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.67 g) is added 10% aqueous sodium hydroxide (7 ml), and the mixture is refluxed for 5 hours. After cooling, the mixture is acidified with diluted hydrochloric acid and is extracted with dichloromethane. The aqueous layer is adjusted to about pH 7.5 with sodium hydrogen carbonate, and the resulting precipitates are recrystallized from ethanol to give 7-morpholino-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.25 g), as pale yellow flakes, m.p. 227.5°-228° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionis extracted with dichloromethane
  4. customthe resulting precipitates
  5. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-8f9db64ee75840bcb90646ac6c3fd904
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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