Hydrochloric Acid → Moxifloxacin hydrochloride

HRID 218345Notes

Reaction equation

HRID 218345 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N:9]2[CH2:17][C@@H:16]3[C@@H:11]([CH2:12][CH2:13][CH2:14][NH:15]3)[CH2:10]2)=[C:7]([F:18])[CH:6]=[C:5]2[C:19]([C:21]([C:27]([OH:29])=[O:28])=[CH:22][N:23]([CH:24]3[CH2:26][CH2:25]3)[C:4]=12)=[O:20].[ClH:30]>CO>[CH3:1][O:2][C:3]1[C:8]([N:9]2[CH2:17][C@@H:16]3[C@@H:11]([CH2:12][CH2:13][CH2:14][NH:15]3)[CH2:10]2)=[C:7]([F:18])[CH:6]=[C:5]2[C:19]([C:21]([C:27]([OH:29])=[O:28])=[CH:22][N:23]([CH:24]3[CH2:26][CH2:25]3)[C:4]=12)=[O:20].[ClH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 152946Moxifloxacin

Product 1

HCID 101526Moxifloxacin hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid-O3,O4 bis(propyloxy-O)borate (100.0 g) was suspended in acetonitrile (445.0 ml). (S,S)-2,8-diazabicyclo(4,3,0)nonane (29.0 g) diluted with 50.0 ml acetonitrile was slowly added at 10-15° C. followed by triethyl amine (25.0 g). The contents were heated to reflux temperature for 2 hours. Cooled to 25-30° C. Methanol (200.0 ml) was added and pH was adjusted to 1.0-2.0 using hydrochloric acid and stirred at 10-15° C. for 2 hours. After the completion of reaction, the reaction mass was concentrated to residue. Purified water 500.0 ml was added and pH was adjusted to 7.5-9.0 using liquour ammonia under stirring. The contents were heated to 70-75° C. and ammonia is expelled off by purging Nitrogen gas to the reaction mass. The reaction mass was cooled to 25-30° C. and stirred for 1 hour. The resulting solid was filtered and washed with purified water and dried under vacuum at 55-60° C. to obtain 75.0 g moxifloxacin base. 70.0 g of moxifloxacin base was stirred with 350.0 ml of methanol at 25-30°. The pH was adjusted to 1.0-2.0 using methanolic hydrochloric acid and contents were chilled to 0-5° C. and stirred for 1 hour at the same temperature. The solid was filtered and dried under vacuum at 85-90° C. to yield 78.0 g (77%) of moxifloxacin hydrochloride.

Workup

  1. filtrationThe solid was filtered
  2. customdried under vacuum at 85-90° C.

Sources & evidence

ORD record
ord-6d22cc11d9314eb39070e68aa4615c02
Source dataset
uspto-grants-2012_06
Patent number
US08198451B2

Reaction notes

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