Sodium Hydroxide → HCID 10473044, compound

HRID 1651388Notes

Reaction equation

HRID 1651388 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:18][C:17]([CH3:20])([OH:19])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:22])[C:6]([C:23]([O:25]CC)=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]4[CH2:16][C:17]([CH3:20])([OH:19])[CH2:18]4)[C:12]=3[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23051774Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-methyl-3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 10473044HCID 10473044, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.9 g (2.9 mmoles) of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 0.54 g (4.3 mmoles) of 3-hydroxy-3-methylazetidine hydrochloride, 1 g (10.8 mmoles) of triethylamine and 10 ml of pyridine is heated under reflux for 10 hours. The product is cooled, and diluted with water. Filtering and washing yields 0.95 g (89%) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-methyl-3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate which is then hydrolysed by heating a mixture of 0.38 g (1 mmole) of this ester with 1.5 ml of ethanol, and 8 ml of 0.5N sodium hydroxide under reflux for 3 hours. The mixture is cooled, filtered and acidified with acetic acid.

Workup

  1. temperaturehydrolysed by heating
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2c65a0cba85441fea88d27f498c1f3ad
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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