Gol. 80 washed neutral with water, then acetone and vacuum dried; yield 3.19 g. The sulfur eliminated as sulfuric acid in the peracetic acid solution corresponded to 2.36% on the weight of I,14 and the product II contained 1.95% S (total sulfur accounted for 100.2%). The product gave 1.75% S by ion-exchange and 0.087% NIL, equivalent to 0.174% S. Total sulfonic acid sulfur was thus 1.92% (98.5% of that present). The product dissolved completely in 90% formic acid at 18°in 3 hours, whereas compound I remained insoluble after 10 weeks. It had a considerably increased affinity for the basic dye methylene blue and a marked decrease in affinity for the acid dye Orange II.The ammonium salt was prepared by adding a few drops of N ammonia solution to 1.0 g. of a preparation of Nmethylene-66-sulfonic acid {Anal. Found: S, 1.09; X, 10.6) and vacuum drying the product. Anal. Caled, for ammonium salt: N, 11.5. Found: X, 11.7.N-Mercaptomethyl-66 Monosulfide (III).-Eight grams of N-mercaptomethyl-66 disulfide (I) (%S 4.30) was allowed to react with 400 ml. of 0.10 M potassium cyanide solution at 65°for 6 hours with occasional shaking. The monosulfide was filtered, washed with water, acetone and vacuum dried; yield 7.79 g. Anal. Found: S, 2.32. This corresponds to 54.0% of the original sulfur. The solution and washings contained thiocyanate equivalent to 46.5% of the original sulfur.16 After reaction with cyanide solution for 20 hours, 46.5% of the sulfur was in the product and 53.7% was in solution.The product III was completely devoid of disulfide sulfur and thiocyanate groups. The latter could not be detected chemically, and the infrared absorption spectrum showed no maximum at 2,000 cm.-116 characteristic of the thiocyanate (14) After 24, 48, 96 and 192 hours reaction with peracetic acid, 53.7, 54.8, 54.4 and 53.3%, respectively, of sulfur was removed from the disulfide as sulfuric acid, showing that equation b represents a terminal reaction.(15) W. W. Scott and N. H. Furman, "Standard Methods of Chemical Analysis," Lancaster Press, Inc., Lancaster, Pa., 1952, p. 277.(16) Determined on a Grubb-Parsons double-beam spectrometer, using the potassium bromide disk technique. See . M. Stimson and M.

Fraction 7 was successfully crystallized in the collection tube, leading to one crop of crystals, m.p. 90-93.5°, easily shown to be identical with an authentic sample of 2,3,4-trimethylquinoline, lit.6 m.p. 90-92°, by the identity of their infrared spectra. A second crop, m.p. 67-75°, isolated in very small yield, was shown by mass spectra (parent peak at mass 171 ± 4) and ultraviolet spectra (long wave-length maxima at 320, 314, and 307 mg) to be a trimethylquinoline. The infrared spectrum showed that substitution had occurred in the benzene ring (absorption at 775 and 820 cm.-1) and in fact the spectrum proved to be identical with that of an authentic sample of 2,4,5-trimethyIquinoline.16 "Butanone Anil" 2,4-Diethyl-2-methyl-l,2-dihydroquinoline. -Aniline and 2-butanone reacted according to the procedure given by Vaughan4 for the preparation of 2,2,4-trimethyl-l,2dihydroquinoline. 2-Butanone (835 g.) was passed into the reaction mixture of aniline (279 g.) and iodine, (9 g.), which was maintained at 170-175°. The product was crudely distilled to separate butanone and the bulk of the aniline, then fractionated on a 4-ft. glass helix column and the fraction, b.p. 170-174°( 28 mm.), 95 g. (lit.18 b.p. 152-153°at 12 mm.), collected. The n.m.r.showed a vinyl resonance at 4.95 , the NH resonance at 6.73 , and a quartet centered at 7.55 t(J = 7.5 c.p.s.), assigned to the methylene group at position 4 of XII.The remainder of the spectrum consisted of the usual aromatic multiplet, a single resonance at 8.82 assigned to the methylene group at C-2 of XII, and a pattern of seven lines interpreted as a triplet centered at 8.87t ( J = 7.5 c.p.s.) overlapped on the low field side by a quartet centered at 8.69 (J = 7.5 c.p.s.) and on the high field side by a triplet centered at 9.13 (/ = 7.5 c.p.s.). The seven line pattern thus represents the two methyl groups attached to methylenes at C-2 and C-4, and the methylene attached to the saturated center at C-2.A sample purified by v.p.c. gave the following analysis.

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