Hydrochloric Acid → Tosufloxacin hydrochloride

HRID 232505Notes

Reaction equation

HRID 232505 reaction equation
C([NH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:33])[C:15]([C:28]([O:30]CC)=[O:29])=[CH:16][N:17]3[C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[CH:12][C:11]=2[F:34])[CH2:6]1)(=O)C.[ClH:35]>>[ClH:35].[NH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:33])[C:15]([C:28]([OH:30])=[O:29])=[CH:16][N:17]3[C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[CH:12][C:11]=2[F:34])[CH2:6]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13652939Ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 10433396Tosufloxacin hydrochlorideYield 84%

Procedure

In 5 ml of 6N hydrochloric acid was dissolved 500 mg of ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and the resulting solution was subjected to reaction under reflux for 4 hours. Subsequently, the crystals thus deposited were collected by filtration and washed with 1 ml of water to obtain 390 mg (yield 84.0%) of 7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride having a melting point of 247°-250° C. (decomp.). The physical properties of this compound were identical with those of the compound obtained in Example 54.

Workup

  1. customthe resulting solution was subjected to reaction
  2. temperatureunder reflux for 4 hours
  3. filtrationSubsequently, the crystals thus deposited were collected by filtration
  4. washwashed with 1 ml of water

Sources & evidence

ORD record
ord-12090108e1914f43b554d136e6b667fc
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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