Ethanol → HCID 14934996, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 cm3 round bottom flask was added 3-ethylaniline (5.0 g, 41.3 mmol), ethanol (7.5 cm3), sodium carbonate (5.9 g, 55.7 mmol). Ethyl iodide (17.38 g, 111.4 mmol) was added dropwise. The mixture was then heated at 45° C. for 12 hours before cooling to room temperature and adding water (50 cm3). The mixture was extracted into diethyl ether (3×50 cm3) the extracts were dried over magnesium sulphate, filtered, and concentrated to give the title compound (7.03 g, 96%) as a light yellow oil. δH (250 MHz; CDCl3): 7.20 (1H, dd, 9, 7.25, ArH), 6.60 (3H, m, ArH), 3.43 (4H, q, 7, NCH2), 2.69 (2H, q, 7.25, CH2), 1.32 (3H, t, 7.5, CH3), 1.23 (6H, t, 7, CH3); δC (62.9 MHz; CDCl3): 12.7 (CH3), 15.8 (CH3), 29.5 (CH2), 44.4 (NCH3), 109.4 (ArC), 111.4 (ArC), 115.1 (ArC), 129.2 (ArC), 145.4 (ArC), 147.9 (ArC).

Provenance & Evidence