Hydrochloric Acid → Tosufloxacin hydrochloride

HRID 246965Notes

Reaction equation

HRID 246965 reaction equation
C([NH:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[C:27]([F:28])=[CH:26][C:13]([C:14]([C:16](=[CH:22]N(C)C)[C:17]([O:19]CC)=[O:18])=[O:15])=[C:12]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])[N:11]=2)[CH2:6]1)(=O)C.[ClH:38]>C(O)C>[ClH:38].[NH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[C:12]3[C:13]([C:14](=[O:15])[C:16]([C:17]([OH:19])=[O:18])=[CH:22][N:29]3[C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])=[CH:26][C:27]=2[F:28])[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70391376ethyl 2-[6-(3-acetylamino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinoyl]-3-(N,N-dimethylamino)acrylate

Product 1

HCID 10433396Tosufloxacin hydrochlorideYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 4 ml of ethanol was suspended 200 mg of ethyl 2-[6-(3-acetylamino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinoyl]-3-(N,N-dimethylamino)acrylate, and 4 ml of 6N hydrochloric acid was added thereto, after which the resulting mixture was subjected to reaction under reflux for 3.5 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 2 ml of ethanol, after which crystals were collected by filtration to obtain 145 mg (yield 85.4%) of 7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 3.5 hours
  4. customSubsequently, the solvent was removed by distillation under reduced pressure
  5. customto the crystalline material thus obtained
  6. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-f67a44ed513245f29f5675c76b5dade9
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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