This is a continuation of the studies in this Laboratory on the reducing action of Grignard reagents.2

The residue above, 37-39, and fractions 7-8 were combined and fractionated through column X to give 5.0 g. of methylneopentylcarbinol, »md 1.4175-1.4195, which gave an -naphthylurethan, m. p. and mixed m. p., 86-87°. This was checked with a 3,5-dinitrobenzoate, m. p. and mixed m. p., 95-95.5°. This sample, together with the 6.6 g. of fractions 40-41, represents a 3.4% yield of reduction product. Attempts to find 2-heptanol were unsuccessful. Fractions 9-17 contained dodecenes (0.63 mole) and fractions 18-30 contained methyl-re-amylneopentylcarbinol.

Mengel6 for the production of 2,4-methylated quinolines: £-aminoethylbenzene (8 g.) and 6.6 g. of acetylacetone were refluxed for thirty minutes and then, for removal of water formed in the reaction, refluxing was continued for fifteen minutes with the condenser steam-heated. After addition of 115 cc. of concentrated sulfuric acid and heating on a steam cone for twenty minutes, the mixture was poured onto ice. The base was liberated with caustic and extracted with ether. Next, diazotization in dilute hydrochloric acid for removal of ^-aminoethylbenzene was carried out in the usual way. After removal of non-basic admixtures by ether extraction, the solution was made alkaline with caustic and the liberated base was extracted with ether. The yield of crude 2,4-dimethyl-6ethylquinoline was 4 g. (33%). The picrate prepared in alcohol solution crystallizes from alcohol in fine needles melting at 190-191°.

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