反应详情

温度

80 °C

A flask was charged with 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-cyano-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 18; 590 mg; 1.53 mmol), hydroxylamine hydrochloride (637 mg; 9.16 mmol) (769 mg; 9.16 mmol) followed by ethanol (15 ml) and the resulting suspension was stirred at 80° C. overnight. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalents of each) were added and the mixture stirred at 80° C. for ca. 14 h. The mixture was cooled to room temperature, and the precipitate was filtered off and the residue washed with ethanol. The combined filtrate and washings were evaporated in vacuo and the residue partitioned between water and ether. The phases were separated and the aqueous phase extracted twice with ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound (547 mg).

1. stirringthe mixture stirred at 80° C. for ca. 14 h
2. temperatureThe mixture was cooled to room temperature
3. filtrationthe precipitate was filtered off
4. washthe residue washed with ethanol
5. customThe combined filtrate and washings were evaporated in vacuo
6. customthe residue partitioned between water and ether
7. customThe phases were separated
8. extractionthe aqueous phase extracted twice with ether
9. dry with materialThe combined organic phases were dried over MgSO4
10. concentrationconcentrated in vacuo