ReductiveN-Monoalkylation of Primary Aromatic Amines

Abstract
Primary aromatic amines 1 with a variety of ring substituents are easily converted to their N-monoalkyl derivatives 3 by a simple variation of the sodium borohydride/sulfuric acid/carbonyl compound procedure previously described for their N-permethylations. The procedure is suitable for the α-monodeuterium labelling of the new N-substituent.

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