Hydrochloric Acid → HCID 15475386, compound

Participants

Reaction Steps

Generally, the diazonium tetrafluoroborate intermediates are prepared by nitration of 7-hydroxycoumarin with nitric acid in sulfuric acid to give 6-nitro-4-8-dimethyl-7-hydroxycoumarin 1 (see Example 1 below) which is then o-allylated by treatment with allyl bromide and potassium carbonate in dimethylsulfoxide to produce 6-nitro-4,8-dimethyl-7-allyloxycoumarin 2 (see Example 2 below). The 6-nitro-4,8-dimethyl-7-allyloxycoumarin is then reduced by treatment with tin(II) chloride, tin, and concentrated hydrochloric acid in ethanol to give 6-amino-4,8-dimethyl-7-allyloxycoumarin 3 (see Example 3 below). Finally, 6-diazoniumtetrafluoroborate-4,8-dimethyl-7-allyloxycoumarin 4 is formed by treatment with sodium nitrite in tetrafluoroboric acid (see Example 4 below).

Provenance & Evidence