Sodium Hydroxide → 3-(Methoxymethyl)-8-quinolinol

HRID 235258

Reaction equation

HRID 235258 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([CH2:12][O:13][CH3:14])=[CH:7]2.[OH-:15].[Na+]>O.[Ta]>[OH:15][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([CH2:12][O:13][CH3:14])=[CH:7]2

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 199579168-Chloro-3-methoxymethylquinoline

Product 1

HCID 110087013-(Methoxymethyl)-8-quinolinolYield 63.2%

Reagents, catalysts & solvents 2

HCID 23956TantalumCatalystHCID 962WaterSolvent

Procedure

Into a tantalum liner in a 600 ml stirred Parr pressure reactor is placed 4.15 g 8-chloro-3-methoxymethylquinoline (20 mmol), 8.0 g 50% aqueous sodium hydroxide (100 mmol) and a solution of 250 mg cupric sulfate pentahydrate (1.0 mmol, 5 mole percent) in 95 ml of water. Sodium hydroxide concentration is 4%. The system is sealed, brought to 160 degrees C and held for 21.5 hours. The cooled solution is filtered through Celite, extracted with two 20 ml portions of toluene, then the aqueous layer is adjusted to pH 3-4 with sulfuric acid and finally to pH 7 with ammonium hydroxide. The mixture is extracted with two 50 ml portions of ethyl acetate. Rotary evaporation of the organic layer gives 2.39 g (63% yield) of crude 8-hydroxy-3-methoxymethylquinoline as a yellow green solid. The crude material is treated with two 500 ml portions of boiling water, leaving behind some insolubles. Long silky yellow needles of pure 8-hydroxy-3-methoxymethylquinoline separate. After filtering and drying, 1.83 g (48% yield) is obtained.

Workup

  1. customThe system is sealed
  2. custombrought to 160 degrees C
  3. filtrationThe cooled solution is filtered through Celite
  4. extractionextracted with two 20 ml portions of toluene
  5. extractionThe mixture is extracted with two 50 ml portions of ethyl acetate
  6. customRotary evaporation of the organic layer

Sources & evidence

ORD record
ord-4a523960b08c4f60b5ac30ef423edd3b
Source dataset
uspto-grants-1997_01
Patent number
US05597924

Linked notes

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