Sodium Hydroxide → 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethenyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

HRID 223153Notes

Reaction equation

HRID 223153 reaction equation
[OH-].[Na+].C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:23]=[C:22]3[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]3[CH:24]=[CH2:25])=[CH:16][C:15]=2[F:30])[CH2:10][CH2:9]1)=O)C>C(O)(=O)C>[F:30][C:15]1[CH:16]=[C:17]2[C:22](=[N:23][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[N:21]([CH:24]=[CH2:25])[CH:20]=[C:19]([C:26]([OH:28])=[O:27])[C:18]2=[O:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13054059HCID 13054059, compound

Product 1

HCID 30579271,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethenyl-6-fluoro-4-oxo-7-(1-piperazinyl)-Yield 80.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1-(2-chloroethyl)-7-(4-ethoxycarboxyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (2.27 g) was dissolved in ethanol (15 ml) by heating, and to the solution was added a solution of potassium hydroxide (0.84 g) in ethanol (15 ml). The resulting solution was heated to reflux for 2 hours with stirring. The resulting crystals were colleced by filtration and washed with ethanol. The crystals were then dissolved in 20 ml of water by heating, and the solution was adjusted to pH 4-5 with 10% acetic acid. The resulting crystals were collected by filtration, washed with ethanol and recrystallized from a mixture of ethanol and chloroform to give 1.74 g of 7-(4-ethoxycarbonyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylic acid (mp 246°-248° C.). Five percent sodium hydroxide solution (30 ml) was added to 1.5 g of 7-(4-ethoxycarbonyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylic acid. The mixture was heated to reflux for 5 hours with stirring. After cooling, the solution was adjusted to pH 7 with acetic acid. The resulting precipitate was collected by filtration. The precipitate was dissolved in aqueous 10% acetic acid under heating, and the solution was adjusted to pH 9 with ammonia solution. The resulting precipitate was collected by filtration to give 0.98 g of 6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-vinyl-1,8-naphthyridine-3-carboxylic acid, m.p. 256°-260° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. dissolutionThe precipitate was dissolved in aqueous 10% acetic acid
  6. temperatureunder heating
  7. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-5e0b459fbff444f0aa62f6f1c1aca76d
Source dataset
uspto-grants-1982_10
Patent number
US04352803

Reaction notes

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