8-HYDROXYQUINOLINES

摘要

1499439 5 - Halo - 8 - hydroxyquinolines GENERAL MILLS CHEMICALS Inc 4 March 1975 [4 March 1974] 8933/75 Heading C2C [Also in Division C1] Novel 5 - halo - 8 - hydroxyquinolines of the general formula in which X is Cl or Br; R is C 8-20 branched chain alkyl or alkenyl and R 1 , R 2 and R 3 are each H or C 1-4 alkyl are prepared by either (a) reacting 5- Cl or Br- 8-hydroxyquinoline with an alkenyl chloride and subsequently heating the mixture to give a compound with R = alkenyl; (b) reacting 8-hydroxyquinoline with alkenyl chloride, subsequently heating and hydrogenating and either chlorinating or brominating the product to give a compound with R = alkyl and (c) reacting 2-amino-4-Cl or Br-phenol with anα,#-unsaturated aldehyde and reacting the product obtained with alkenyl chloride to give a compound with R=alkenyl and R 1 and/or R 2 and/or R 3 = alkyl. Amongst the examples 5-chloro-7-dodecyl-8-hydroxyquinoline and 2 - methyl - 5 - bromo - 7 - dodecenyl- 8-hydroxyquinoline are prepared. 7 - Dodecenyl - 8 - hydroxyquinoline is obtained by reacting 8-hydroxyquinoline with dodecenyl chloride in the presence of NaOH and KI. 7 - Dodecyl - 8 - hydroxyquinoline is obtained by hydrogenation of the latter over Pd/C. 3 - Methyl - 5 - chloro - 8 - hydroxyquinoline is prepared by reacting 2-amino-4-chlorophenol, 2 - nitro - 4 - chlorophenol and methacrolein in the presence of ferrous sulphate and cone. H 2 SO 4 . 4 - Methyl - 8 - hydroxyquinoline is produced by reacting o-aminophenol with methyl vinyl ketone in polyphosphoric acid.