Ciprofloxacin → HCID 13326837, compound

HRID 1284510Notes

Reaction equation

HRID 1284510 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[CH:25]([C:27]([CH3:29])=[O:28])=[CH2:26]>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:26][CH2:25][C:27](=[O:28])[CH3:29])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 2764CiprofloxacinHCID 6570Methyl vinyl ketone

Product 1

HCID 13326837HCID 13326837, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.31 g (0.01 mol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid and 3.9 g of methyl vinyl ketone are heated under reflux in 50 ml of ethanol for 2 hours. The solid is filtered off with suction and washed with methanol to give 2.5 g (62.3% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(3-oxobutyl)-1-piperazinyl]-3-quinolinecarboxylic acid of decomposition point 185°-187° C.

Workup

  1. filtrationThe solid is filtered off with suction
  2. washwashed with methanol

Sources & evidence

ORD record
ord-011f6c1167a149a59a65efe1baf3a349
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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