Hydrochloric Acid → HCID 15712730, compound

HRID 1073762Notes

Reaction equation

HRID 1073762 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:23])[C:10]([F:22])=[C:11]([N:14]4[CH2:19][CH2:18][N:17](C=O)[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:24])[C:6]([CH:25]=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.Cl>>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:23])[C:10]([F:22])=[C:11]([N:14]4[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]4)[CH:12]=3)[C:7](=[O:24])[C:6]([CH:25]=[O:26])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 15712728HCID 15712728, compound

Product 1

HCID 15712730HCID 15712730, compoundYield 51.5%

Procedure

To 1-cyclopropyl-6-fluoro-7-(4-formyl-1-piperazinyl)-5-methyl-3-formyl-1,4-dihydro-4-oxoquinoline (1.2 g) is added 3N hydrochloric acid (15 ml) and the mixture is refluxed for 1 hour. After distilling off hydrochloric acid under reduced pressure, water is added to the resulting residue. The mixture is made weakly alkaline with saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The chloroform layer is washed with water, dried over sodium sulfate, and the chloroform is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent, chloroform → chloroform : methanol =50 : 1) and recrystallized from ethanol to give 1-cyclopropyl-6-fluoro-7-(1-piperazinyl)-5-methyl-3-formyl-1,4-dihydro-4oxoquinoline (0.57 g), as pale yellow powdery crystals, m.p. 21020 -213° C. (dec.).

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. distillationAfter distilling off hydrochloric acid under reduced pressure, water
  3. additionis added to the resulting residue
  4. extractionextracted with chloroform
  5. washThe chloroform layer is washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe chloroform is distilled off under reduced pressure
  8. customThe resulting residue is purified by silica gel column chromatography (eluent, chloroform → chloroform : methanol =50 : 1)
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b365ca8e66774c88bc59f27578e1695e
Source dataset
uspto-grants-1990_11
Patent number
US04971970

Reaction notes

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