Water → 1-Cyclopropyl-6,7-difluoro-8-(1-hexinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 129412Notes

Reaction equation

HRID 129412 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([F:20])[C:12]=3[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7](=[O:22])[C:6]([C:23]([O:25]CC)=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.O.S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([F:20])[C:12]=3[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 131719206Ethyl 1-cyclopropyl-6,7-difluoro-8-(1-hexinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 1317192071-Cyclopropyl-6,7-difluoro-8-(1-hexinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.7 g of ethyl 1-cyclopropyl-6,7-difluoro-8-(1-hexinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate is refluxed for 3 hours in a mixture of 6 ml of glacial acetic acid, 0.5 ml of water and 0.1 ml of concentrated sulphuric acid. The reaction mixture is treated with 100 ml of water, and the solid is filtered off with suction and dried. 0.5 g of 1-cyclopropyl-6,7-difluoro-8-(1-hexinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is obtained (85% of theory).

Workup

  1. filtrationthe solid is filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-39c7cd47782d4524bff800bd6d8b19da
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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