Hydrochloric Acid → 1-Cyclopropyl-6,8-difluoro-7-[2-(dimethylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.hydrochloride

HRID 477863Notes

Reaction equation

HRID 477863 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:15]4[CH2:20][CH2:19][O:18][CH:17]([CH2:21][N:22]([CH3:24])[CH3:23])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:26])[C:6]([C:27]([O:29]CC)=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.[ClH:32]>O.C(O)C>[ClH:32].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:15]4[CH2:20][CH2:19][O:18][CH:17]([CH2:21][N:22]([CH3:24])[CH3:23])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14652597Ethyl 1-cyclopropyl-6,8-difluoro-7-[2-(dimethylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 146525981-Cyclopropyl-6,8-difluoro-7-[2-(dimethylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.hydrochlorideYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.21 g of ethyl 1-cyclopropyl-6,8-difluoro-7-[2-(dimethylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylate and 5 ml of concentrated hydrochloric acid in 10 ml of water and 10 ml of ethanol is refluxed, for 2.5 hours. The resultant mixture is concentrated under reduced pressure and to the obtained crystals is added ethanol. The crystals are filtered off with suction, washed with ethanol and then dried to give 1.82 g of 1-cyclopropyl-6,8-difluoro-7-[2-(dimethylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.hydrochloride in 80% yield, melting at 267°-268° C.

Workup

  1. concentrationThe resultant mixture is concentrated under reduced pressure and to the obtained crystals
  2. additionis added ethanol
  3. filtrationThe crystals are filtered off with suction
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-af4e4df0f73c4cb598a1039574a1f1f3
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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