Potassium Carbonate → HCID 14651165, compound

HRID 2396987Notes

Reaction equation

HRID 2396987 reaction equation
C(OC([NH:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[C:21]([CH3:22])=[C:20]3[C:15]([C:16](=[O:31])[C:17]([C:26]([O:28]CC)=[O:27])=[CH:18][N:19]3[CH:23]3[CH2:25][CH2:24]3)=[C:14]([CH3:32])[C:13]=2[F:33])[CH2:8]1)=O)C.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[NH2:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[C:21]([CH3:22])=[C:20]3[C:15]([C:16](=[O:31])[C:17]([C:26]([OH:28])=[O:27])=[CH:18][N:19]3[CH:23]3[CH2:25][CH2:24]3)=[C:14]([CH3:32])[C:13]=2[F:33])[CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 21801009HCID 21801009, compound

Product 1

HCID 14651165HCID 14651165, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To ethyl 7-(3-ethoxycarbonylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (130 mg) is added 5% aqueous potassium hydroxide solution (3.2 ml) and the mixture is refluxed for 4 hours. After cooling, the reaction mixture is made acidic with acetic acid and then made weak alkaline with potassium carbonate. The resultant is extracted with dichloroethane and the extract is dried, followed by distillating the solvent under reduced pressure. To the residue is added diethyl ether and the precipitated crystals are filtered to give 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg), m.p. 96°-98° C., as pale yellow needles.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. extractionThe resultant is extracted with dichloroethane
  4. customthe extract is dried
  5. additionTo the residue is added diethyl ether
  6. filtrationthe precipitated crystals are filtered

Sources & evidence

ORD record
ord-b031f6f060a9406baf97decc8d0c9478
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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