232. Quinamine. Part IV. Sulphobenzeneazoquinamine and nitration and oxidation of quinamine to 3 : 6 : 8-trinitro-4-hydroxyquinoline

Bis(chloromethyl) Ether

“…InChI = 1/C2H4Cl2O/c3-1-5-2-4/h1-2H2 InChIKey = HRQGCQVOJVTVLU-UHFFFAOYAN (useful reagent for the chloromethylation of aromatic moieties 1 and for the preparation of oxygen-containing heterocycles 2 ) Alternative Name: BCME; α,α -dichloromethyl ether; 1,1dichloromethyl ether; chloromethyl ether; oxybis(chloromethane); sym-dichloromethyl ether. Physical Data: bp 106 • C; mp −41.5 • C; d 1.315 g cm −3 .…”

“…1 The procedure was reported to be superior to chloromethylation using paraformaldehyde and hydrogen chloride, which afforded only poor yields of the desired anisole. Bis(chloromethyl) ether is an effective reagent for the direct chloromethylation of a variety of aromatic substrates.…”

Alkaloids

“…in which R may be H as in cinchonine, ·OH as in cupreine or ·OCH 3 as in quinine and quinidine, and R′ is the vinyl group (·CH: CH 2 ) in the four principal cinchona alkaloids and becomes (CH 2 ·CH 3 ) in their reduction products such as hydroquinine. Variation on this general formula is however beginning to appear as the minor cinchona alkaloids, of which there are about twenty, come under more detailed investigation and recently it has been shown that in quinamine, and so possibly in cinchonamine, although vinylquinuclidine is present, the normal quinoline portion of the cinchona alkaloid structure is replaced and the nature of the replacement, possibly an indole derivative, is under discussion 22 …”