Sulfuric Acid → HCID 19841136, compound

HRID 1638675Notes

Reaction equation

HRID 1638675 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)[C:12]=3[CH2:14][OH:15])[C:7](=[O:24])[C:6]([C:25]([O:27][CH2:28]C)=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[C:35](=O)([O-])O.[Na+]>CO>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]4)[C:12]=3[CH2:14][O:15][CH3:35])[C:7](=[O:24])[C:6]([C:25]([O:27][CH3:28])=[O:26])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 19841143HCID 19841143, compound

Product 1

HCID 19841136HCID 19841136, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-cyclopropyl-7-(4-methyl-1-piperazinyl)-6-fluoro-8-hydroxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (160 mg) in methanol (10 ml) is added conc. sulfuric acid (2 ml), and the mixture is refluxed for 6.5 hours. The reaction mixture is adjusted to below pH 8 with aqueous saturated sodium hydrogen carbonate and extracted with dichloromethane. The extract is washed with aqueous saturated sodium chloride and then dried over magnesium sulfate and the solvent is distilled off. The residue is crystallized by adding thereto diethyl ether to give methyl 1-cyclopropyl-7-(4-methyl-1-piperazinyl)-6-fluoro-8-methoxymethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (125 mg), as pale yellow powder, m.p. 200°-204° C.

Workup

  1. temperaturethe mixture is refluxed for 6.5 hours
  2. extractionextracted with dichloromethane
  3. washThe extract is washed with aqueous saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off
  6. customThe residue is crystallized
  7. additionby adding

Sources & evidence

ORD record
ord-e332d393f3d944099c8e16a7a5488541
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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