Water → 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylic acid

HRID 129421Notes

Reaction equation

HRID 129421 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([F:19])[C:12]=3[C:14]#[C:15][C:16]([CH3:18])=[CH2:17])[C:7](=[O:21])[C:6]([C:22]([O:24]CC)=[O:23])=[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:20])=[C:11]([F:19])[C:12]=3[C:14]#[C:15][C:16]([CH3:18])=[CH2:17])[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 88439967Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylate

Product 1

HCID 884354121-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.715 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylate is refluxed for 1.5 hours in a mixture of 10 ml of glacial acetic acid, 0.5 ml of water and 0.2 ml of concentrated sulphuric acid. The reaction mixture is poured into 100 ml of water. The solid which has precipitated is filtered off with suction, washed with water and dried. 0.53 g of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(3-methyl-but-3-en-1-inyl)-4-oxo-3-quinolinecarboxylic acid is obtained (80% of theory).

Workup

  1. customThe solid which has precipitated
  2. filtrationis filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-54e54e8be367473894a2d6ecba00d9f7
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

Loading…