Sodium Hydroxide → HCID 19363338, compound

HRID 850431Notes

Reaction equation

HRID 850431 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:20][C:21]([O:23]CC)=[O:22].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53702022HCID 53702022, compound

Product 1

HCID 19363338HCID 19363338, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-chloro-7-methoxy-8-pentyloxyquinoline-3-carbamate (311 mg, 0.84 mmol), ethanol (3 ml) and a 1N aqueous sodium hydroxide solution (3 ml) were mixed, and this solution was refluxed under heating for 0.5 hour. Ethanol was evaporated under reduced pressure, and conc. hydrochloric acid was added to make the reaction mixture acidic. THF (10 ml) and ethyl acetate (10 ml) were added to dissolve the precipitated crystals. The organic layer was separated, washed 3 times with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethanol to give 4-chloro-7-methoxy-8-pentyloxyquinoline-3-carbamic acid (229 mg, 80%) as pale-yellow crystals.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 0.5 hour
  3. customEthanol was evaporated under reduced pressure, and conc. hydrochloric acid
  4. additionwas added
  5. additionTHF (10 ml) and ethyl acetate (10 ml) were added
  6. dissolutionto dissolve the precipitated crystals
  7. customThe organic layer was separated
  8. washwashed 3 times with saturated brine (10 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe drying agent was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-93610d3a71674beeb54b34cdad8b07bb
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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