Acetic Acid → 1-Cyclopropyl-7-fluoro-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1084400Notes

Reaction equation

HRID 1084400 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:19]5[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:26])[C:6]([C:27]([O:29]CC)=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.C(O)(=O)C>C(O)C.[OH-].[K+].O>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:19]5[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 14853346HCID 14853346, compound

Product 1

HCID 147005741-Cyclopropyl-7-fluoro-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 50.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 0.85 g of 1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-(4-methyl-1-pip-erazinyl)-4 -oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 12 cm3 of ethanol, 5 cm3 of 2 N aqueous potassium hydroxide solution and 7 cm3 of water is heated at a temperature close to 80° C. for 1 hour. After adding 5.8 cm3 of a 10% aqueous solution of acetic acid, the precipitate obtained is drained and washed with 3 times 5 cm3 of water. After recrystallizing twice from a mixture of 7.5 cm3 of ethanol and 7.5 cm3 of dimethylformamide each time, 0.4 g of 1-cyclopropyl-7-fluoro-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid melting at 250° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 80° C. for 1 hour
  3. customthe precipitate obtained
  4. washwashed with 3 times 5 cm3 of water
  5. customAfter recrystallizing twice from a mixture of 7.5 cm3 of ethanol and 7.5 cm3 of dimethylformamide each time

Sources & evidence

ORD record
ord-948a5d8083b94684b71cbf9f710c02e5
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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