Réaction #2446121
ord-d7272b9af19d4e2faed4af44fa61c82a
Équation de réaction
8-hydroxyquinoline
hydrochloric acid
formaldehyde
→
5-chloromethyl-8-hydroxyquinoline
Réactifs
Aucun
Conditions de réaction
Conditions détaillées
See reaction.notes.procedure_details.
Mode opératoire
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.