Acetate → 1-Cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 47890Notes

Reaction equation

HRID 47890 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([Cl:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([O:21]C)=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.C([O-])(=O)C.S(=O)(=O)(O)O>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([Cl:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 175AcetateHCID 1118Sulfuric AcidHCID 23431770Methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 104256071-Cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28.6 g of methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.088 mol), 160 ml of acetate acid, 100 ml of water and 18 ml of concentrated sulfuric acid were stirred for 40 minutes at 100-110° C. The resulting mixture was cooled and filtered. The precipitate was re-crystallized from choroform-ethanol to afford 25.2 g of 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Gaticarboxylic acid, 0.081 mol) in 91.8% yield, mp 195-199° C.

Workup

  1. temperatureThe resulting mixture was cooled
  2. filtrationfiltered
  3. customThe precipitate was re-crystallized from choroform-ethanol

Sources & evidence

ORD record
ord-8632f70cb72443d0a76c0ea95c5c2000
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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