SYNTHESIS OF 4-ALKOXYQUINOLINES FROM QUINOLINE REISSERT COMPOUNDS

Article abstract of DOI:10.3987/COM-91-5945

The quinoline Reissert compound (5a) was converted to 1-benzoyl-3-bromo-2-cyano-1,2,3,4-tetrahydro-4-methoxyquinoline (6a) by successive treatment in methanol with bromine and aq. sodium carbonate.Hydrolysis of 6a with hydrochloric acid gave 3-bromoquinoline (4; R=H), but that with aq. sodium hydroxide afforded 4-methoxyquinoline (7a).Reissert compounds derived from some quinoline derivatives (5) gave the corresponding 4-methoxyquinolines (7) through tetrahydroquinolines (6) in a similar way.