The Chemistry of 2h-3,1-Benz0xazine-2,4(1h)-Di0ne (Isatoic Anhydride). 23 (1). Synthesis of 2-(2-Propenyl)- And 2-Isopropylanelines

Abstract

Isatoic anhydrides react with excess methyllithium at -78°C to produce tertiary alcohols 2 in high yields. The hydroxyl group of 2 can be dehydrated to give the 2-(2-propenyl)anilines 111 using iodine under azeotropic water removal conditions. Catalytic hydrogenation of the olefin affords the target 2-isopropylaniline derivatives 11. 95 c Η CI 81 84 d CH 3 CI 49 94 303