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A novel reaction of ammonium chloride and α-aromatic amine carboxaldehydes

✍ Scribed by Elie Abushanab

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
148 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel reaction was discovered when ammonium chloride was used to catalyze the formation of pyrazine carboxaldehye dimethyl acetal**from pyraxine carboxaldehye (1) and methyl orthoformate. In addition to the desired product (40%) another crystalline basic yellow compound m. p. 202-203 was formed in 10% yield. Elemental analysis supported an empirical formula of C10H,N5. The infrared data indicated the lack of significant functional groups and the ultraviolet spectrum had the following maxima at 348 (6 =lSOOO) and 252 (6 = 22400). *** The mass spectrum analysis exhibited abundant peaks at m/e 197 (MC. 100%); m/e 196 (M+-1. 6%); m/e 170 (M+-27. 12%); m/e 143 (M+-27-27, 30%). It indicated an odd number of nitrogen atoms and a mode of fragmentation typical for unsubstituted aromatic nitrogen heterocycles (2). The n. m. r. chemical shifts in neutral and acidified (CF3CGGH) deuterochloroform as well as the results of proton decoupling experiments leading to their assignments are listed in Table .

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