Norfloxacin → 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(1-chloroethoxy carbonyl)-1-piperazinyl]-3-quinoline carboxylic acid

HRID 845722

Reaction equation

HRID 845722 reaction equation
[CH3:1][CH2:2][N:3]1[C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:41]([O:43][CH:44]([Cl:46])[CH3:45])=[O:42]>C(Cl)(Cl)Cl>[CH2:2]([N:3]1[C:9]2[C:8](=[CH:13][C:12]([F:14])=[C:11]([N:15]3[CH2:20][CH2:19][N:18]([C:41]([O:43][CH:44]([Cl:46])[CH3:45])=[O:42])[CH2:17][CH2:16]3)[CH:10]=2)[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:1]

Participants

5

Reactant 3

HCID 4539NorfloxacinHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 148012951-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(1-chloroethoxy carbonyl)-1-piperazinyl]-3-quinoline carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Norfloxacin (6.4 g) was suspended in 300 ml of chloroform and 4.3 g of proton sponge® was added to it. The suspension was cooled in an ice bath and 4.0 g of 1-chloroethyl chloroformate was added. A clear solution resulted in half an hour. The reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated in vacuum to about 150 ml. The crystals formed were filtered and washed with chloroform. The pure product weighed 5.3 g.

Workup

  1. temperatureThe suspension was cooled in an ice bath
  2. customA clear solution resulted in half an hour
  3. concentrationThe reaction mixture was concentrated in vacuum to about 150 ml
  4. customThe crystals formed
  5. filtrationwere filtered
  6. washwashed with chloroform

Sources & evidence

ORD record
ord-d21d2f084c1942dc921e756a6a7f225b
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Linked notes

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