Hydrochloric Acid → 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-(1,1-dimethylethyl)-6-fluoro-4-oxo-7-(1-piperazinyl)-

HRID 1031559Notes

Reaction equation

HRID 1031559 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O>[N:18]1([C:11]2[N:10]=[C:9]3[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]3[C:24]([CH3:27])([CH3:25])[CH3:26])=[CH:13][C:12]=2[F:17])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14839606HCID 14839606, compound

Product 1

HCID 4618761,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-(1,1-dimethylethyl)-6-fluoro-4-oxo-7-(1-piperazinyl)-Yield 67.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This ester 400 mg (1.06 mmoles) was suspended in 1 mL water, 1,9 mL 1N aqueous sodium hydroxide was added. The suspension was refluxed 30 minutes. The solution was cooled and adjusted to pH 7.5 with 1N hydrochloric acid. The precipitate was filtered and washed with water. The crude product was recrystallized in water to give 248 mg of titled compound. MP>270° C.

Workup

  1. temperatureThe suspension was refluxed 30 minutes
  2. temperatureThe solution was cooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customThe crude product was recrystallized in water

Sources & evidence

ORD record
ord-5d84adb1d7b24c7ea9b2eb7b2f324b28
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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