Ethanol → Dianiline

Participants

Reaction Steps

4-Amino-3-nitrophenylacetic acid (0.82 g) and the product from Example 16 (0.91 g) were treated by the procedure described in Example 19. The intermediate product was hydrogenated using a palladium catalyst in ethanol to yield the intermediate dianiline. Treatment of this intermediate with formic acid (1.2 equivalents) in 10% aqueous hydrochloric acid at reflux for 1 hour, followed by isolation and conversion to the bis-methanesulfonate salt yielded 0.63 g of the desired product as a white solid. m.p. 128°-130° C. 1H NMR (CDCl3, 300 MHz) of the free base δ1.4-1.8 (m, 3H), 2.1 (m, 1H), 2.4 (s, 3H), 2.3-3.0 (m, 9H), 3.2 (m, 1H), 3.79 (s, 3H), 6.6 (dd, 1H), 6.8 (t, 1H), 7.16 (dd, 1H), 7.48 (bs, 1H), 7.59 (bs, 1H), 8.02 (s, 1H). Anal calcd for C24H34FN3O7S2.H2O: C, 49.90; H, 6.28; N, 7.27. Found: C, 49.68; H, 6.00; N, 7.10.

Provenance & Evidence