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

HRID 2372072Notes

Reaction equation

HRID 2372072 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]4)[N:12]=3)[C:7](=[O:26])[C:6]([C:27]([O:29]CC)=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]4)[N:12]=3)[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13565843HCID 13565843, compound

Product 1

HCID 4654511,8-Naphthyridine-3-carboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.7 g (1.6 mmole) of ethyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(ethoxycarbonyl)-1-piperazinyl]-1,8-naphthyridine-3-carboxylate, 6 ml of 10% aqueous sodium hydroxide and 2 ml of ethanol was refluxed for three hours. The reaction was filtered through a fiber glass pad to clarify and acidified to pH 1.5 with 6.0M hydrochloric acid and lyophilized. The residue was dissolved in 10 ml of ammonium hydroxide and the solution concentrated in vacuo. The precipitate which formed was removed by filtration, washed with aqueous ethanol, ether, and dried in vacuo to give 0.04 g, mp 274-276° C.

Workup

  1. temperaturewas refluxed for three hours
  2. filtrationThe reaction was filtered through a fiber glass pad
  3. dissolutionThe residue was dissolved in 10 ml of ammonium hydroxide
  4. concentrationthe solution concentrated in vacuo
  5. customThe precipitate which formed
  6. customwas removed by filtration
  7. washwashed with aqueous ethanol, ether
  8. customdried in vacuo
  9. customto give 0.04 g, mp 274-276° C.

Sources & evidence

ORD record
ord-1df0c8f4a2944828b1f8b00f0a1da08d
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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