Sodium Carbonate → 4-(5-Amino-6-methylisoquinolin-1-ylamino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence