522638-27-3Relevant articles and documents
Simple synthesis of 7-formyl-indole
Uchil, Vinod R.,Gund, Machhindra,Satyam, Apparao
, p. 1051 - 1056 (2006)
A simple route to 7-formyl-indole (5) is described in which appropriately functionalized o-nitrotoluenes (1) are converted to 7-hydroxymethyl-indole (4) using the Batcho-Leimgruber process. Condensation of 3-methyl-2-nitrobenzyl alcohol (1a) with N,N-dimethylformamide dimethyl acetal yields the enamine 2a, which upon catalytic hydrogenation affords 4 in 22% yield. When the hydroxyl function in 1 is protected with pivaloyl or tetrahydropyranyl group, the yields of 4 are increased to 39% and 48%, respectively. Finally, 4 is oxidized with pyridinium chlorochromate (PCC) to afford 5 in 86% yield. Copyright Taylor & Francis Group, LLC.
