Synthesis of N-alkyl derivatives of 4-(2′-aminoethyl)indole

N-Substituted 4-(2′-aminoethyl)indoles are attainable in good yields from indole-4-acetic acid ( 2 ). Several methods of preparation for 2 were tried or considered. A new sequence involving Arndt-Eistert homologation of indole-4-carboxylic acid has been devised, which is no more laborious than a literature homologation sequence involving indole-4-acetonitrile, and which provides somewhat better overall yields than the literature method.