Hydrochloric Acid → HCID 69547431, compound

HRID 1250010Notes

Reaction equation

HRID 1250010 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([CH3:36])[C:11]([C:17]3[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([CH2:24][N:25]4C(=O)C5C(=CC=CC=5)C4=O)[CH:18]=3)=[CH:12][CH:13]=2)[N:8]([CH:37]2[CH2:39][CH2:38]2)[CH:7]=1)=[O:5])C.[OH-].[Na+].[ClH:42]>CO>[ClH:42].[NH2:25][CH2:24][C:19]1[CH:18]=[C:17]([C:11]2[C:10]([CH3:36])=[C:9]3[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]3[CH:37]3[CH2:38][CH2:39]3)=[CH:13][CH:12]=2)[CH:22]=[C:21]([CH3:23])[N:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69547167HCID 69547167, compound

Product 1

HCID 69547431HCID 69547431, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 0.31 g of 1-cyclopropyl-7-{2-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-6-methyl-4-pyridyl}-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ethyl ester in 2 ml of methanol was added 1.78 ml of an aqueous 1 mol/l sodium hydroxide solution and the mixture was stirred at room temperature for 1 hour. The reaction mixture was adjusted to pH 5.3 with 1 mol/l hydrochloric acid and then precipitated crystals were filtered. The obtained crystals were dissolved in 6 mol/l hydrochloric acid and the solution was stirred with heating at 100° C. for 4 hours. After cooling the reaction mixture to room temperature, insoluble matter was filtered off. The filtrate was concentrated under reduced pressure. Ethanol was added to the obtained residue and precipitates were filtered to obtain 0.15 g of 7-[2-(aminomethyl)-6-methyl-4-pyridyl]-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride. The obtained hydrochloride was dissolved in a mixed solvent consisting of 1.2 ml of ethanol and 1.2 ml of water. After adding 1.2 ml of an aqueous 1 mol/l sodium hydroxide solution to the resulting solution, carbon dioxide gas was blown therein. Filtration of the precipitates afforded 0.10 g of colorless crystals of 7-[2-(aminomethyl)-6-methyl-4-pyridyl]-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid.

Workup

  1. customprecipitated crystals
  2. filtrationwere filtered
  3. dissolutionThe obtained crystals were dissolved in 6 mol/l hydrochloric acid
  4. stirringthe solution was stirred
  5. temperaturewith heating at 100° C. for 4 hours
  6. temperatureAfter cooling the reaction mixture to room temperature
  7. filtrationinsoluble matter was filtered off
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. additionEthanol was added to the obtained residue
  10. customprecipitates
  11. filtrationwere filtered

Sources & evidence

ORD record
ord-8c2965d315de405a957bc257f368942c
Source dataset
uspto-grants-2002_01
Patent number
US06335447B1

Reaction notes

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