Hydrochloric Acid → 6-methyl-5-nitroisoquinolin-1(2H)-one
반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.C1C[O:20]CC1>>[CH3:12][C:8]1[C:7]([N+:13]([O-:15])=[O:14])=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2](=[O:20])[NH:3][CH:4]=[CH:5]2참가 물질
4
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- 온도
- 22 °C
실험 절차
1-chloro-6-methyl-5-nitroisoquinoline (50 g, 225 mmol) was suspended in THF (500 mL, 10 mL/g) and treated with 5 N aq HCl (500 mL, 10 mL/g). The suspension was stirred vigorously in a 2 L Morton Flask under a reflux condenser and heated with a heating mantle to reflux overnight (14 h). The resulting suspension was allowed to cool to room temperature (22° C.). The solid was removed by suction filtration and the filtrate set aside. The solid was washed with water (100 mL), Et2O (2×100 mL) and hexane (100 mL), then air-dried to afford 40 g as a light yellow powder. The reserved filtrate was concentrated in vacuo to a volume of ˜500 mL to afford a second crop of product. The second crop was washed with water (100 mL), Et2O (2×100 mL) and hexane (100 mL), then air-dried to afford 4 g as an orange powder. A total of 44 g (87% yield) of the title compound were isolated in this fashion. MS (M+H)+ 205.