Studies on Tetrahydroisoquinolines. IV. Synthesis of 4-Alkyl (phenyl) amino-7-hydroxy-6-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolines

Reaction of 4, 7-diacetate (I) in a variety of aqueous amine solution was found to give the corresponding 4-alkylamino derivatives (Va-e or Vg-1) in good yield. In the case of aniline, however, the presence of potassium hydroxide was always required. Similar reaction with aqueous semicarbazide or thiosemicarbazide solution containing potassium carbonate or hydroxide afforded the corresponding 4-hydrazino derivatives (Vm or Vn) in good yield.