Journal of Organic Chemistry p. 4983 - 4987 (1986)
Update date:2022-09-26
Topics: React the benzamide with an amine to form an imine Reduce the imine to the amine using a reducing agent such as sodium borohydride (NaBH4) or another suitable reagent
Schultz, Arthur G.
Macielag, Mark
In contrast to literature suggestions, benzonitriles and N,N-dialkylbenzamides are excellent substrates for Birch reduction and reductive alkylations.Thus, o-methoxybenzonitrile (1a) and benzonitrile (1b) give 1,4-cyclohexadienes 2a-2d from alkali-metal reduction in NH3-THF with tert-butyl alcohol (1 equiv), followed by sequential addition of an alkyl halide and excess NH4Cl.The product of HCN elimination
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