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54, 1977 (1932). 241 J. E. A. Otterstedt and R. Pater, J. Heterocycl. Chem. 9,225 (1972). 239 240 32 LINDSAY A. SUMMERS [Sec. A (42) to 4,7-bis-2'-cyanoethyl- 1,2,3,4,7,8,9,10-octah ydro- 1,10-dioxo-4,7phenanthroline (43) with aluminum chloride and hydrochloric acid in c h l o r o b e n ~ e n eThe . ~ ~ ~structure was confirmed spectroscopically and by reaction with hydrazine, which gave the tetraazapyrene derivative (44). '~ IV. General Reactions A. REDUCTION 1. IJO-Phenanthroline The reduction of 1,lO-phenanthroline (4) occurs preferentially in the pyridine rings.
F. Elslager and F. H. Tendick, J. Med. Pharrn. Chem. 5,546 (1962). 24 LINDSAY A. SUMMERS [Sec. D C. 12 It was obtained pure in low yield (-4%) along with 2,8-phenanthroline (- 35%). 1,g-Phenanthroline was subsequently obtained in 34% yield by a Skraup synthesis from 8aminoisoquinoline. l 5 This reaction has been used by others. l B 1 D. 182 The original synthesis of 1,lOphenanthr~line~ by a double Skraup reaction on o-phenylenediamine using glycerol and sulfuric acid in the presence of an oxidizing agent continues to attract attention, and various improvements in reaction I** J.
C. Evans, and E. H. Godden, J. Chem. Soc. B, 149 (1970). Z75 J. Mlochowski, Rocz. Chem. 48,2145(1974). 272 38 LINDSAY A. SUMMERS [Sec. C 3. 1 ,I 0-Phenanthroline Reports of further studies of the nitration of 1,lO-phenanthroline have appeared. 252 A much milder route to 5-nitro- 1,lO-phenanthroline involves nitration of the tris-phenanthroline complex of cobalt(II1) which is readily nitrated in concentrated sulfuric acid at 80". 252In this way 3-nitro- 1,lO-phenanthroline was obtained in very low yield.