1969 Volume 17 Issue 1 Pages 140-144
On the reaction of 5-, 6-, 7-, and 8-nitroquinoline with potassium cyanide in methanol solution, always two kinds of compound were obtained in a moderate yield. The one was o-methoxyquinoline-carbonitrile, in which the cyano group is introduced in ortho-position to the nitro group and then the nitro group is replaced by a methoxyl group, and the other was 1-aminosoxazoloquinoline, in which the nitro group was reduced to hydroxyamino group and this hydroxyamino group was cyclized to an isoxazole ring with the cyano group introduced at ortho-position of the original nitro group. However, in the reaction of 4-nitroquinoline, 4-methoxyquinoline was obtained as a sole product.
