Ethanol → 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-6-fluoro-1-(2-fluoroethyl)-4-oxo-7-(1-piperazinyl)-

HRID 2413123Notes

Reaction equation

HRID 2413123 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:28])[C:15]([C:23]([O:25]CC)=[O:24])=[CH:16][N:17]3[CH2:20][CH2:21][F:22])=[CH:12][C:11]=2[F:29])[CH2:6][CH2:5]1)(=O)C.C(O)C>Cl>[F:29][C:11]1[CH:12]=[C:13]2[C:18](=[N:19][C:10]=1[N:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1)[N:17]([CH2:20][CH2:21][F:22])[CH:16]=[C:15]([C:23]([OH:25])=[O:24])[C:14]2=[O:28]

Participants

4

Reactant 2

HCID 702EthanolHCID 20430478HCID 20430478, compound

Product 1

HCID 30690021,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-6-fluoro-1-(2-fluoroethyl)-4-oxo-7-(1-piperazinyl)-Yield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of the above ester (4.8 g) in 10% hydrochloric acid (48 ml) is heated for 2 hours on a steam-bath. After cooling, an appropriate amount of ethanol is added to the mixture to precipitate crystals, which are collected by filtration, dissolved in water (about 50 ml), treated with active charcoal, and filtered. The filtrate is adjusted to pH 7.5-8 with 10% aqueous ammonia to give 3.5 g of 6-fluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid (m.p. 223°-225° C.).

Workup

  1. temperatureis heated for 2 hours on a steam-bath
  2. temperatureAfter cooling
  3. customto precipitate crystals, which
  4. filtrationare collected by filtration
  5. dissolutiondissolved in water (about 50 ml)
  6. additiontreated with active charcoal
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f49e54dd7e7e48368038de7dd40a9511
Source dataset
uspto-grants-1985_01
Patent number
US04496566

Reaction notes

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