Moxifloxacin difluoro methoxy ethyl ester → 1-Cyclopropyl-6,7-difluoro-8-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 2356380Notes

Reaction equation

HRID 2356380 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14]C)[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=[O:20])=[CH:5]2)[CH2:3][CH2:2]1>Br.C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[OH:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 10758239Moxifloxacin difluoro methoxy ethyl ester

Product 1

HCID 116807371-Cyclopropyl-6,7-difluoro-8-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 89.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

The preparation comprises dissolving Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (10.0 g, 30.9 mmol) in 40% HBr aqueous solution (20 mL) and acetic acid (20 mL) to react at 100° C., charging reaction mixture into ice water (500 mL) under fast stirring after the reaction finishes, going on with the stirring for 0.5 h, filtering, and drying obtained filter cake to give 1-cyclopropyl-6,7-difluoro-8-hydroxy-1,4-dihydro-oxoquinoline-3-carboxylic acid (7.8 g, 89.6%).

Workup

  1. customto react at 100° C.
  2. customstirring for 0.5 h
  3. filtrationfiltering
  4. customdrying
  5. customobtained
  6. filtrationfilter cake

Sources & evidence

ORD record
ord-41eeed3c861a4e169441e5ed565efd7a
Source dataset
uspto-grants-2010_07
Patent number
US07759362B2

Reaction notes

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