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

HRID 129410Notes

Reaction equation

HRID 129410 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[C:14]#[CH:15])[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=[O:20])=[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:17])=[C:11]([F:16])[C:12]=3[C:14]#[CH:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 19371453Ethyl 1-cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 152891331-Cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.3 g of ethyl 1-cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are refluxed for 4 hours in a mixture of 100 ml of glacial acetic acid, 8 ml of water and 3 ml of concentrated sulphuric acid. After cooling to room temperature, the solid is filtered off with suction, washed with water and dried. In this way, 5.7 g of 1-cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (62% of theory) are obtained.

Workup

  1. filtrationthe solid is filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0f6e7f2980cd4b95ab4388331fb38bda
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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