反应详情

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.

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