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lions, except that the sublimtatiou of the crude product, required a longer time (2 days, 60°oil bath) and the sublimate was recrystallized from EtzO-low boiling petr ether; 25% yield; nip 87.5 ,S9°. Anal. (C,0H,NBrF) C, , N.General Procedure for Preparation of Urea and Thiourea Derivatives of 3-Aminoisoquinolines 22, 23,24.--The urea derivatives were prepared by condensation of the 3-aminuisoquinolilies with the corresponding isocyanates and isothiocyanates in warm CeH6 solutions (several days). The yields (purified) were 85% for 22, 01 % for 23, and 30% for 24. liecrystallization solvents and elements analyzed are given in Table I.General Procedure for Preparation of Sulfonamides of 3-Ammoisoquinolir.es. -The sulfonamides 18, 20, and 21 were obtained by heating at ca. 00°the aminoisoquinolines with the corresponding sulfonyl chlorides in pyridine, 'fire yields of purified materials were 5(1% for 18, 90% for 20, and 55% for 21 I!, 1). and F. Karan 'filie acetamide 20 was deacetylated in a refluxing (30 mini mi.xi lire of EtOH-concd HCI (5: 1) for 30 min and the sulfa nil,amide 19 was isolated in ca. 60% yield as the free liase."-( 3-Isoquinolyl )crotonamide ( 15).• -In aunt tempt to aminate ,Y-i3-isoqmnolyl)-3-ehlorobutyramide1 with excess of ,Y,.\dimethyl-.Y'-ethylethylenediamine in refluxing CHCfii only the elimination product .Y-(3-isoquiiiolyI icrotonamide was isolated (48%), mp 150-132°(Table I).-Y-(3-Isoquinolyl)acrylamide ( 14). This compound was isolated as tlie elimination product of .V-(3-isoquiiu:>lyl)-3-ohloro-propionamide1 with PhNHMe in refluxing CHCl, in tlie presence of Na-XO:, (Table U. 3-Benzamidoisoquinolines. -A'-(3-lsoquinolyljbenzamiile i l(i) and .\'-('3-isoquinoiyl)-3-nitmbenzamide (17) were obtained in fair yields by the reactions of 3-aminoqiiiiioliiie with the nppmpriale benzoyl rliiiirides in refluxing ('«Hr, íTable 11.

Large quantities of pure glycamines were conveniently prepared by the reductive alkylation of ammonia or by the hydrogenolysis of N-benzylglycamines. To ensure high quality products, purification of the glycamines from either process should be carried out through their Schiff bases.Although 1-amino-l-deoxy sugars, the glycamines, have been known for over fifty years, a good preparative method which is practical for the synthesis of large quantities of high purity material is not available. The need for large quantities of galactamine of greater than 95% purity as a resolving agent in a synthesis of pantothenic acid2 prompted us to reinvestigate the preparation of this class of compounds.Glycamines previously have been prepared by the chemical reduction of sugar oximes,3-5 by electrolytic, chemical and catalytic reduction of gly-cosylamines5 and by the reductive alkylation of ammonia with a sugar.6-8 The chemical and electrolytic reduction methods were of little interest because they were not readily adaptable to large-scale operations. The Flint and Salzburg7 method yielded impure sirups unsuitable for our purposes.

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