Hydrochloric Acid → 5-(Chloromethyl)quinolin-8-ol

Participants

Reaction Steps

As shown in Scheme A below, 8-hydroxyquinoline (A1) is treated with hydrochloric acid and formaldehyde to give 5-chloromethyl-8-hydroxyquinoline (A2). The chloro group of A2 is substituted with propargylamine to afford 5-(1-propargylamino)methyl-8-hydroxyquinoline (A3). Bromination of A3 employing N-bromosuccinimide (NBS) provides the bromide A4 which is then treated, for example, with the modified peptide [D-Cys6]GnRH to give the target compound A5, which is the compound M22A in Appendix I.

Provenance & Evidence