Ammonia → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-

HRID 2291282

Reaction equation

HRID 2291282 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[NH3:28]>>[NH2:28][C:9]1[C:10]([F:22])=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]2)[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 143003861-Cyclopropyl-5,6,8-trifluoro-7-(3-methyl 1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 30666843-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-4-oxo-

Conditions

Temperature
100 °C

Procedure

A mixture of 1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (150 mg) and 28% aqueous ammonia (15 ml) was heated at 100° C. for 48 hours in a sealed tube. The reaction mixture was evaporated to dryness under reduced pressure and water was added to the residue. The mixture was extracted with chloroform. After drying, the extract was evaporated and the residue was recrystallized from chloroform-ethanol to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (93 mg), m.p. 251°-253° C.

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. customAfter drying
  5. customthe extract was evaporated
  6. customthe residue was recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-4575fc5a058c45d5937cee72a5349250
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Linked notes

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