反应详情

温度

70 °C

A mixture of 4-(6-methyl-5-nitroisoquinolin-1-ylamino)benzonitrile (0.47 g, 1.5 mmol), tin(II) chloride dihydrate (1.8 g, 7.7 mmol) and absolute EtOH (50 mL) was stirred under N2 at 70° C. for 17 h. The crude reaction mixture was poured onto ˜100 mL ice. The resulting solution was treated with solid Na2CO3 to pH 10. The milky yellow suspension was extracted with EtOAc (3×150 mL). The combined EtOAc extracts were washed with saturated NaCl (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 510 mg as a red solid. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 5% MeOH in CH2Cl2, to provide 4-(5-amino-6-methylisoquinolin-1-ylamino)benzonitrile (0.29 g, 68% yield) as a red solid. MS (ESI, pos. ion) m/z: 275 [M+H]+.

1. customThe crude reaction mixture
2. extractionThe milky yellow suspension was extracted with EtOAc (3×150 mL)
3. washThe combined EtOAc extracts were washed with saturated NaCl (100 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give 510 mg as a red solid
8. customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
9. washeluting with a gradient of 1% to 5% MeOH in CH2Cl2