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Bromination of 6‐methoxy‐5,8‐quinolinedione gave the 7‐bromo derivative in quantitative yield. Treatment of the bromo compound with sodium azide followed by hydrogenation yielded 7‐amino‐6‐methoxy‐5,8‐quinolinedione, the A‐B ring portion of the antitumor antibiotic strep tonigrin. The corresponding 2‐methyl homolog was prepared in a similar manner from 6‐methoxy‐2‐methyl‐8‐nitroquinoline, which in turn, was obtained by a Skraup synthesis from 2‐nitro‐anisidine and crotonaldehyde.

MethylglyoxalBi.s-(gcanylhydrazoxes) 283 2-Methylthio-2-imidazoline Hydrochloride.-A mixture of 209.5 g. (2.05 moles) of ethylenethiourea, 120 ml. (2.36 moles) of methyl chloride, and 250 ml. of methanol was heated in a stainless steel bomb at 100°for 3 hr. The reaction mixture was filtered to obtain 196 g. of material melting at 166-169°. The filtrate was diluted with ether to obtain an additional 92.5 g. of product, m.p. 161-166°. Total yield was 288.5 g. (92%).

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