Sodium Iodide → HCID 10610946, compound

Participants

Reaction Steps

A mixture of 5-methoxy-3-methyl-2-nitrophenol [J. Atkinson et al., J. Org. Chem. 56, 1991, 1788-1800](5.00 g, 27.3 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (4.33 g, 30 mmol), K2CO3 (15.1 g, 109 mmol), NaI (0.41 g, 2.7 mmol), an butanone (50 mL) was heated at reflux for 1 h then cooled to room temperature. A mi8xture of 2-dimethylaminoethyl chloride hydrochloride (4.33 g, 30 mmol), K2CO3 (7.6 g, 54.6 mmol), and butanone (15 mL) that had been shaken for 5 min was added and the mixture was heated at reflux for 1.5 h. The mixture was concentrated and the remaining slurry was diluted with water and extracted with EtOAc (×4). The combined extracts were washed with 2 N aqueous Na2CO3 (×10) and extracted with 2 N aqueous HCl (×5). The combined extracts were washed with EtOAc, made basic with Na2CO3, and extracted with EtOAc (×4). These extracts were dried (MgSO4) and evaporated to give 2-(5-methoxy-3-methyl-2-nitrophenyloxy)-N,N-dimethylethanamine (4.38 g, 63%) as a yellow oil; 1H NMR (CDCl3) δ 6.38 (d, J=2.4 Hz, 1 H, H-6'), 6.32 (d, J=2.4 Hz, 1 H, H-4', 4.12 (t, J=5.8 Hz, 2 H, OCH2), 3.81 (s, 3 H, OCH3), 2.73 (t, J=5.8 Hz, 2 H, NCH2), 2.31 (s, 6 H, N(CH3)2), 2.28 (s, 3 H, 3(--CH3); 13C NMR δ 161.0 (C-5'), 151.8 (C-1'), 136.1 (C-2'), 132.7 (C-3'), 106.7 (C-4'), 97.9 (C-6'), 68.1 (OCH2), 57.4 (NCH2), 55.5 (OCH3), 45.8 (N(CH3)2), 17.7 (3'--CH3). Calc. for C12H18N2O4, M+254.1267. Found, 254.1276. Starting material (1.178 g, 24%) was recovered from the basic washes by acidification and extraction.

Provenance & Evidence