Acetic Acid → 1-Cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid

HRID 1266169Notes

Reaction equation

HRID 1266169 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:31])=[C:15]([N:19]5[CH2:24][CH2:23][N:22]([CH2:25][C:26]6[O:30][CH:29]=[CH:28][CH:27]=6)[CH2:21][CH2:20]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:32])[C:6]([C:33]([O:35]CC)=[O:34])=[CH:5]2)[CH2:3][CH2:2]1.C(O)(=O)C>C(O)C.[OH-].[K+]>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:31])=[C:15]([N:19]5[CH2:20][CH2:21][N:22]([CH2:25][C:26]6[O:30][CH:29]=[CH:28][CH:27]=6)[CH2:23][CH2:24]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:32])[C:6]([C:33]([OH:35])=[O:34])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18549171Ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

Product 1

HCID 99130381-Cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acidYield 49.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 1.5 g of ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was heated, with stirring, at a temperature around 80° C. for approximately 1 hour 30 in 15 cm3 of ethanol and 14 cm3 of 1 N potassium hydroxide solution, 32 cm3 of 5% acetic acid were added at this same temperature and the suspension was stirred for 20 minutes. After recrystallizing from a mixture of 15 cm3 of dimethylformamide and 15 cm3 of ethanol, 0.7 g of 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was obtained in the form of a yellow solid melting at about 241° C.

Workup

  1. temperaturewas heated
  2. customAfter recrystallizing from a mixture of 15 cm3 of dimethylformamide and 15 cm3 of ethanol

Sources & evidence

ORD record
ord-d8731429e1534a13b79a9aa7d1042288
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

Loading…