2-Ethylaniline → N,N′-(2,6-Pyridinediyldiethylidyne)bis[2-ethylbenzenamine]

Participants

Reaction Conditions

Reaction Steps

One g of 2,6-diacetylpyridine and 3.0 ml of 2-ethylaniline were added to a round-bottom flask with 30 ml of methanol. A stirbar and 5 drops of 97% formic acid were added, and the flask was sealed and the solution was stirred for 24 hours at 50° C. The flask was then cooled to room temperature and placed in a freezer at −30° C. After 1 day, yellow crystals had formed. The crystals were isolated by filtration and identified by 1H NMR as the desired product (1.25 g, 55.2%). 1H NMR (CDCl3): δ 8.38 (d, 2, Hpyr), 7.86 (t, 1, Hpyr) 7.20 (m, 4, Haryl), 7.07 (t, 2, Haryl), 6.65 (d, 2, Haryl) 2.49 (q, 4, Hbenzyl), 2.35 (s, 6, N—C—CH3), 1.14 (t, 6, CH2CH3).

Provenance & Evidence