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Synthesis of galegine

K. Babor and I. Ježo

Slovak Academy of Sciences, Bratislava

 

Abstract: A synthesis of galegine from 4-methyl-2-pentenoic acid (I) is described. Doebner condensation of Me2CHCHO with CH2(CO2H)2 gives 73% I, b12 105-7°. Refluxing I in KOH-EtOH yields 87% 4-methyl-3-pentenoic acid (II), b12 100-2°. II with SOCl2 forms 89% II acid chloride (III), b12 58-9° which with NaN3 gives Me2C:CHCH2CON3, which in abs. EtOH gives 71% Me2C:CHCH2NHCO2Et (IV), b14 97-100°, nD22.5 1.4460. Hydrolysis of IV with conc. HCl yields 48% Me2C:CHCH2NH2.HCl (V), decomp. 193-4°; picrate, decomp. 139-40°. V is also prepd. in 42% yield by Curtius rearrangement of III. Condensation of V with EtSC(:NH)NH2.HBr in dil. H2SO4 gives 60% Me2C:CHCHNHC(:NH)NH2.1/2H2SO4, decomp. 227°.

Full paper in Portable Document Format: 81a18.pdf (in Slovak)

 

Chemical Papers 8 (1) 18–21 (1954)

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