An Efficient and Practical Synthesis of N,N-Diethyl-7-indolyloxyacetamide via 7-Hydroxyindole

Abstract

An efficient and practical synthesis of N,N-diethyl-7-indolyloxyacetamide (1) from 3-hydroxy-2-nitrotoluene (4) via 7-hydroxyindole (2) is described. Treatment of 3-benzyloxy-2-nitrotoluene (5) obtained from 4 with DMF dimethyl acetal and pyrrolidine afforded the (E)-2-nitro-β-pyrrolidinostyrene 6, which can be readily converted into the 2-nitrophenylacetaldehyde semicarbazone 7 without isolation of 6. Hydrogenation of 7 over Pd/C, followed by reaction of the resulting 2 with 2-chloro-N,N-diethylacetamide produced 1 in good yield.