3-Bromoaniline → HCID 18548970, compound

Participants

Reaction Steps

4-Chloro-6-ethoxyl-[1,5]naphthyridine-3-carbonitrile (500 mg, 2.14 mmol) was heated at reflux with m-bromoaniline (0.69 ml, 3 eq) in the presence of pyridine HCl salt (250 mg, 1.1 eq) in ethoxyethanol (20 ml) under argon for 3 hrs. After cooling the mixture was diluted with water, made basic with NH4OH, and extracted with CH2Cl2. The extracts were washed (Brine), dried (Na2SO4), and concentrated. The remaining solid was triturated with a mixture of CH2Cl2 and ether, giving the title compound as a yellow solid. mass spectrum (electrospray, m/e): 370.9 (M+H); IR cm-1: 3305, 2217; H-NMR δ (DMSO-d6): 1.365 (3H, t, CH3), 4.585 (2H, q, CH2), 7.327 (1H, d, C8-H), 7.395 (2H, m, C4′ and C6 Hs in bromoaniline), 7.503, (1H, m, C5′-H), 7.618 (1H, s, C2′-H), 8.194 (1H, d, C7-H), 8.516 (1H, s, C2-H), 9.684 (1H, bs, NH).

Provenance & Evidence