Hydrochloric Acid → 8-Hydroxy-5,6,7,8-tetrahydroquinoline

HRID 2301141Notes

Reaction equation

HRID 2301141 reaction equation
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.Cl.[OH-].[Na+]>>[OH:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 122262495,6,7,8-Tetrahydroquinolin-8-yl acetate

Product 1

HCID 118159398-Hydroxy-5,6,7,8-tetrahydroquinolineYield 100%

Procedure

8-Acetoxy-5,6,7,8-tetrahydroquinoline (630 mg, 3.3 mmol) was mixed with 10% hydrochloric acid aqueous solution and stirred overnight while heating under reflux. After returning to room temperature, this was neutralized with sodium hydroxide aqueous solution and the reaction product was extracted with chloroform. The extract was washes with saturated brine and dried with anhydrous sodium sulfate and then the solvent was removed by evaporation under a reduced pressure to obtain 490 mg (3.3 mmol, 100%) of the title compound.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customAfter returning to room temperature
  4. extractionthe reaction product was extracted with chloroform
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure

Sources & evidence

ORD record
ord-c8af7354d2fe443eb2b195f76e7e3e76
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…