Studies with Reissert Compounds. Part VI. Change of Pathway Occasioned by Phase Transfer Catalysis: Suppression of N-Acyl Pseudo-base Formation in Favour of a Reissert Reaction

Abstract

Treatment o f phthalazine w i t h p-chlorobenzoyl chloride and potassium cyanide i n a two-phase system gives an 1-acyl pseudobase (3, R = 4-ClCsH4).Addition o f a phase t r a n s f e r c a t a l y s t t o the medium changes the reaction pathway t o give a Reissert compound (4, R = 4-C1C6H4) as major product w i t h only a trace o f N-acyl pseudo-base.The same change i s observed w i t h 5 -n i t r o -isoquinoline and a v a r i e t y o f a c i d chlorides.Inclusion o f a ( a ) Satisfactory elemental analyses and spectral data obtained.(b) l i t .m.p. 1480C9 ( c ) l i t .m.p. 83-850c1° (d) 1it.m.p. 60-6l0c11 ( e ) l i t .m.p. 127-1280c12