Aniline → HCID 178501725, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of aniline (2.52 mL) in 6M HCl (15 mL) is added dropwise a solution of NaNO2 (2.44 g) in water (8 mL) at -10° C. The solution stirs at 0° C. for 1 h and is poured into a solution of methyl 3-(2-chloro-5-(4-morpholinylmethyl)-3-thienyl)-3-oxopropanoate (Preparation 64, 3.50 g) in pyridine (15 mL) and water (8 mL) with vigorous stirring at −10° C. The solution stirs at 0° C. for 60 min and is diluted with cold water (150 mL). The aqueous layer is extracted with EtOAc (3×150 mL). The organic layers are combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude red liquid (2.93 g) is utilized without any further purification. Physical characteristics: IR (liq.) 1737, 1675, 1529, 1455, 1437, 1330, 1306, 1263, 1239, 1218, 1201, 1168, 1144, 1117, 755 cm−1; MS (FAB) m/z 422 (MH+); HRMS (FAB) m/z 422.0935 (C19H20ClN3O4S+H).

Provenance & Evidence