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Synthesis 1995; 1995(12): 1534-1538
DOI: 10.1055/s-1995-4131
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Synthesis of 5-Alkoxy-4-alkylamino-1,2-benzoquinones

Loïk Viallon* , Olivia Reinaud, Patrice Capdevielle, Michel Maumy
  • *Laboratoire de Recherches Organiques de l’ESPCI, associé au CNRS, 10 rue Vauquelin, F-75231 Paris 05, France
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Publication History

Publication Date:
31 December 2000 (online)

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A simple and efficient method is described for a general synthesis of 4-dialkylamino-5-methoxy-1,2-benzoquinones 3 which involves, in polar solvents, a regioselective (>95%) nucleophilic monosubstitution by a wide range of secondary alliphatic amines on an easily prepared 1,2-quinone 1. Regioselectivity is not observed in the reaction of primary amines with 1, but a further reaction with an alcohol in basic medium allows valorization of the undesirable product.

1,2-benzoquinones - aminoquinones - nucleophilic substitution by amines - regioselectivity