Ethyl Acetate → N-(6-mercaptoisoquinolin-1-yl)benzamide

Participants

Reaction Steps

A solution of NaOH (92 mg) in water H2O (1 ml) was added to a solution of dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester (70 mg) in MeOH (1 ml) and THF (1 ml). The mixture was stirred for 1 h at ambient temperature then for a further 1 h at 56° C. The organics were removed in vacuo then the mixture was diluted with water and acidified with dilute hydrochloric acid (pH ˜3.5). The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) and concentrated in vacuo to give a residue. Flash chromatography of the residue (eluent: 1-5% ethyl acetate in heptane) gave N-(6-mercaptoisoquinolin-1-yl)-benzamide as a yellow residue (30 mg).

Provenance & Evidence