Formation of 3-Aminophenols from Cyclohexane-1,3-diones

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 center dot 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.

Automated summary

meta-Aminophenols are formed by treating 3-amino-2-chlorocyclohex-2-en-1-ones with DBU in MeCN at room temperature, and the chloro compounds are generated by using the halogenating agent BnNMe3·ICl2 in MeOH-CH2Cl2. The amino group must have two substituents, such as two aryl or one aryl and one alkyl group, which can be easily prepared from cyclohex-2-en-1-one and a primary or secondary amine.