Preparation of 1-(3-Aminopropyl)indoles.-The 3-indol-1-ylpropionitrile (1 g.) was reduced in methanol (100 ml.) with freshly prepared Raney nickel (0.5 g.) and hydrogen (60 lbJin.2) in a Pam low pressure hydrogenation apparatus for 6 hr. The Raney nickel was removed by filtration and repeatedly washed with methanol. The methanol was removed under reduced pressure to give the 1-(3-amino-propy1)indole as a colourless semi-solid mass. This was
705 is regarded as Part I of this series. t In a personal communication Dr. Hughes informs us that he and his colleagues are in agreement with this conclusion.
Various substituted 2-hydroxymethylindoles have been prepared by lithium aluminium hydride reduction of corresponding 2-ethoxycarbonylindoles and oxidised with activated manganese dioxide to the respective indole-2-carbaldehydes. Some of the aldehydes have been prepared from the 2-ethoxycarbonylindoles by the McFadyen and Stevens procedure and the two methods are compared. The aldehydes were condensed with nitromethane and nitroethane and the condensation products reduced with lithium aluminium hydride to obtain 2-(2-aminoethyl)-and 2-(2-aminopropyl)-indoles.
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