Ethanol → HCID 14989598, compound

HRID 1110063Notes

Reaction equation

HRID 1110063 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[C:15]3[C:10]([C:11](=[O:27])[C:12]([C:22]([O:24]CC)=[O:23])=[CH:13][N:14]3[CH:18]([CH3:21])[CH2:19]Cl)=[CH:9][C:8]=2[F:28])[CH2:3]1.C(O)C.[OH-].[K+]>O>[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[C:15]3[C:10]([C:11](=[O:27])[C:12]([C:22]([OH:24])=[O:23])=[CH:13][N:14]3[C:18]([CH3:21])=[CH2:19])=[CH:9][C:8]=2[F:28])[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14989580HCID 14989580, compound

Product 1

HCID 14989598HCID 14989598, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

159 mg (0.38 mmol) of ethyl 7-(3-amino-1-pyrrolidinyl)-1-(1-chloroprop-2-yl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Compound No.1) prepared in Example 1 was dissolved into 20 ml of ethanol. To this was added 65 mg (1.15 mmol) of pulverized potassium hydroxide and the mixture was heated under refluxing for 14 hours. 3 ml of water was added and the mixture was heated under refluxing for a further 3 hours. After cooling, the reaction mixture was concentrated under reduced pressure, the residue was washed with water, and dried to obtain a crude product. The crude product was purified by silica gel column chromatography (chloroform:methanol=5:1) to obtain 52 mg of light yellow crystals of 7-(3-amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-4-oxo-1-(prop-1-en-2-yl)-quinoline-3-carboxylic acid (Compound No. 19).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 14 hours
  3. temperaturethe mixture was heated
  4. temperatureunder refluxing for a further 3 hours
  5. temperatureAfter cooling
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. washthe residue was washed with water
  8. customdried
  9. customto obtain a crude product
  10. customThe crude product was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-f990a1a4ece74feea777befc9be5349c
Source dataset
uspto-grants-1994_06
Patent number
US05324735

Reaction notes

Loading…