Hydrochloric Acid → 1-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid hydrochloride

HRID 246983Notes

Reaction equation

HRID 246983 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:17]=2)[C:12](=[O:26])[C:11]([C:27]([O:29]CC)=[O:28])=[CH:10]1.O.[ClH:33]>>[ClH:33].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:17]=2)[C:12](=[O:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13849334Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 136529841-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid hydrochlorideYield 93.2%

Procedure

In 1.2 ml of 6N hydrochloric acid was suspended 200 mg of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate, and the resulting suspension was subjected to reaction under reflux for 2 hours. Subsequently, 2 ml of water was added thereto and crystals were collected by filtration and washed with 1 ml of water to obtain 190 mg (yield 93.2%) of 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid hydrochloride having a melting point of 249°-252° C. (decomp.).

Workup

  1. customthe resulting suspension was subjected to reaction
  2. temperatureunder reflux for 2 hours
  3. filtrationcrystals were collected by filtration
  4. washwashed with 1 ml of water

Sources & evidence

ORD record
ord-d9e5ce0d2bf3480fabad7116e3c18f1a
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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