Hydrochloric Acid → Tosufloxacin hydrochloride

HRID 232503Notes

Reaction equation

HRID 232503 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:16]=[C:15]3[C:10]([C:11](=[O:30])[C:12]([C:25]([O:27]CC)=[O:26])=[CH:13][N:14]3[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:9][C:8]=2[F:31])[CH2:3]1.O.[ClH:33]>>[ClH:33].[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:16]=[C:15]3[C:10]([C:11](=[O:30])[C:12]([C:25]([OH:27])=[O:26])=[CH:13][N:14]3[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:9][C:8]=2[F:31])[CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13667039Ethyl 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 10433396Tosufloxacin hydrochlorideYield 90.2%

Procedure

In 6 ml of 6N hydrochloric acid was suspended 1.00 g of ethyl 7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, and the resulting suspension was subjected to reaction under reflux for 2 hours. Subsequently, 6 ml of water was added thereto and crystals were collected by filtration, and then washed with 2 ml of water to obtain 920 mg (yield 90.2%) 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 suspension was subjected to reaction
  2. temperatureunder reflux for 2 hours
  3. filtrationcrystals were collected by filtration
  4. washwashed with 2 ml of water

Sources & evidence

ORD record
ord-d2f1e00df85647879037e87539eb1a7e
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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