Ethanol → Dinaline

Participants

Reaction Steps

4-Amino-3-nitrophenylacetic acid (0.97 g) and the product from Example 15 (1.0 g) were treated by the procedure described in Example 19. The intermediate product was hydrogenated over palladium in ethanol to yield the intermediate dianiline. Treatment of this intermediate with 2,3-dihydroxy-1,4-dioxane, followed by conversion to the methanesulfonate addition salt yielded 0.88 g. of the desired product. m.p. 192° C. 1H NMR (DMSO-d6, 300 MHz) δ1.7-2.0 (m, 4H), 2.3 (s, 3H), 2.4-3.6 (m, 9H), 3.03 (d, 3H), 3.79 (s, 3H), 6.84 (d, 1H), 6.90 (d, 1H), 7.16 (t, 1H), 7.85 (dd, 1H), 8.1 (m, 2H), 8.96 (m, 2H), 9.1 (bs, 1H). Anal calcd for C24H31N3O4S: C, 62.99; H, 6.83; N, 9.18. Found: C, 62.79; H, 6.96; N, 9.00.

Provenance & Evidence