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

HRID 129417Notes

Reaction equation

HRID 129417 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:18])=[C:11]([F:17])[C:12]=3[C:14]#[C:15][CH3:16])[C:7](=[O:19])[C:6]([C:20]([O:22]CC)=[O:21])=[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:18])=[C:11]([F:17])[C:12]=3[C:14]#[C:15][CH3:16])[C:7](=[O:19])[C:6]([C:20]([OH:22])=[O:21])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 131719208Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylate

Product 1

HCID 1317192091-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.4 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylate are refluxed for 1 hour in a mixture of 20 ml of glacial acetic acid, 1.5 ml of water and 0.5 ml of concentrated sulphuric acid. The mixture is treated with approx. 10 ml of water, and the solid which has precipitated is then isolated and dried. In this manner, 1.05 g of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylic acid are obtained (82% of theory).

Workup

  1. customthe solid which has precipitated
  2. customis then isolated
  3. customdried

Sources & evidence

ORD record
ord-1d84583d1c394e8181493188b1c289b1
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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