Hydrochloric Acid → HCID 14652600, compound

HRID 477865Notes

Reaction equation

HRID 477865 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:29])=[C:11]([N:15]4[CH2:20][CH2:19][O:18][CH:17]([CH2:21][N:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:30])[C:6]([C:31]([O:33]CC)=[O:32])=[CH:5]2)[CH2:3][CH2:2]1.Cl>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:29])=[C:11]([N:15]4[CH2:20][CH2:19][O:18][CH:17]([CH2:21][N:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:30])[C:6]([C:31]([OH:33])=[O:32])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14652583HCID 14652583, compound

Product 1

HCID 14652600HCID 14652600, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.93 g of ethyl 1-cyclopropyl-6,8-difluoro-7-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylate obtained by Example 49(1), 5 ml of 18% aqueous hydrochloric acid in 50 ml of ethanol is refluxed for 7 hours. The reaction mixture is concentrated under reduced pressure, to the obtained residue is added 50 ml of chloroform and the solution is washed with water. After drying over anhydrous magnesium sulfate, the chloroform is distilled off under reduced pressure and the obtained crystals are recrystallized from a mixed solvent of ethyl acetate and isopropyl ether to give 3.53 g of 1-cyclopropyl-6,8-difluoro-7-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in 76% yield, melting at 128°-131° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, to the obtained residue
  2. additionis added 50 ml of chloroform
  3. washthe solution is washed with water
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe chloroform is distilled off under reduced pressure
  6. customthe obtained crystals are recrystallized from a mixed solvent of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-7efe9bcaf74e4ece83d8ab1a493627fb
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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