I. F. Bel'skii, Z. K. Minashkina, O. G. Kesarev
Sep 1, 1970
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Journal
Russian Chemical Bulletin
Abstract
1. 5-Methylfurfurylamine was obtained in 80% yield from 5-methyl-2-furaldehyde by reductive animation. 2. 1-(5-methylfuryl)-2-aminoethane was synthesized by the condensation of 5-methyl-2-furaldehyde with nitromethane and subsequent reduction of the nitro compound with lithium aluminum hydride to the corresponding amine. 3. A study was made of the catalytic hydrogenolysis of 1-(5-methylfuryl)-2-aminoethane and 5-methylfurfurylamine when they were subjected to vapor-phase hydrogenation over Pt/C catalyst at normal hydrogen pressure and a temperature of 230°. 4. Hydrogenolysis of the furan ring under these conditions proceeds mainly at the C-O bond adjacent to the aminoalkyl substituent. 5. α-Pipecoline, 2, 5-dibutylpyrazine, and 2-methylhexamethyleneimine were obtained by a new method, namely by the catalytic hydrogenolysis of 5-methylfurfurylamine and 1-(5-methylfuryl)-2-aminoethane.