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

HRID 980736Notes

Reaction equation

HRID 980736 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 and acidified to pH 1.5 with 6.0 M 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 to and
  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-420e9fa36d4f49caa153d0acdedff7af
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

Loading…