meta-Aminophenols are formed by the action of
DBU on 3-amino-2-chlorocyclohex-2-en-1-ones at room temperature in
MeCN. The chloro compounds are generated by treating 3-aminocyclohex-2-en-1-ones
with the easily prepared halogenating agent BnNMe3·ICl2 in MeOH-CH2Cl2. The amino group must
carry two substituents, either two aryl, one aryl and one alkyl, or
two alkyl groups; 3-aminocyclohex-2-en-1-ones of this type are readily
made from cyclohex-2-en-1-one and a primary or secondary amine.
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