反应详情

Trifluoroacetic acid (17.4 g) was added in one portion to a solution of 5,6,7,8-tetrahydro-5-methyl-2-(phenylmethoxy)-quinolin-5-ol (41 g), phenylmethoxyamine (47 g), and toluene (770 ml) at room temperature. The solution was stirred at room temperature for 24 hrs, and then quenched with concentrated ammonium hydroxide solution. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over potassium carbonate, filtered, and the filtrate was concentrated. Purification by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) gave 44.2 g (77%) of 5,6,7,8-tetrahydro-5-methyl-N,2-bis(phenylmethoxy)-5-quinolinamine.

1. customquenched with concentrated ammonium hydroxide solution
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over potassium carbonate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customPurification
9. washby high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)