Phosphoric Acid → N-(6-methylthioquinolin-5-yl)-2-bromodecanamide

Participants

Reaction Steps

To a stirred solution of 2-bromodecanoic acid (184 mg, 0.73 mmol) in CH2Cl2 (3.0 ml) was injected by syringe oxalyl chloride (0.06 ml, 105 mol %) and then DMF (1 drop). After stirring at room temperature for 1 hour, N-methyl morpoline (0.24 ml, 300 mol %) was added. To this mixture was injected a solution of 5-amino-6-methylthioquinoline (139 mg, 100 mol%) in CH2Cl2 (2.0 ml). After stirring at room temperature for an additional 30 min. the reaction mixture was diluted with CH2Cl2 (30 ml), poured over 1.0M H3PO4 (100 ml), and extracted with CH2Cl2 (3×30 ml). The combined extracts were dried (Na2SO4), evaporated, and chromatographed using 1% triethylamine: ethyl acetate as eluants to give the title compound (192 mg, 62% yield).

Provenance & Evidence