Ammonia → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

HRID 373528Notes

Reaction equation

HRID 373528 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[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:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]2)[CH2:3][CH2:2]1.[NH3:26]>>[NH2:26][C:9]1[C:10]([F:20])=[C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:12]=[C:13]2[C:8]=1[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 148802151-Cyclopropyl-5,6-difluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 30788553-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

Procedure

1-Cyclopropyl-5,6-difluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 28% aqueous ammonia were heated at 100° C. for 48 hours in a sealed tube. The reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in a 1N aqueous solution of sodium hydroxide, and neutralized with a 10% aqueous solution of acetic acid. The crystals which precipitated were collected by filtration to give 5-amino-1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 214°-216° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in a 1N aqueous solution of sodium hydroxide
  3. customThe crystals which precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-364be7f9b54344c68c480f2d4e418b46
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

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