Iodine → Ammonia

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methoxybenzaldehyde (0.895 ml) in t-BuOH (30 ml) was added ethylenediamine (0.546 ml) at room temperature. After 30 min K2CO3 (3.05 g) and I2 (2.330 g) were added then the mixture was heated to 70° C. After 4 h the mixture was diluted with saturated aqueous Na2SO3 and extracted with CHCl3 (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated. Flash column chromatography (gradient, 0-10% MeOH/CHCl3 saturated with NH3) gave 2-(3-methoxyphenyl)-4,5-dihydro-1H-imidazole as a pale yellow oil which solidified under vacuum (1.05 g): 1H-NMR (500 MHz, CDCl3) δ 7.38 (m, 2 H), 7.32 (t, J=8.3 Hz, 1 H), 7.01 (m, 1 H), 6.90 (br, 1 H), 3.78 (s, 3 H), 3.59 (br, 2 H), 2.50 (t, J=1.71 Hz, 2 H).

Provenance & Evidence