8-Aminoquinoline → HCID 41661718, compound

Participants

Reaction Steps

A mixture of 4-iodobenzoic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (9.26 g, 37.3 mmol), DIEA (13.05 mL, 74.7 mmol), HATU (7.10 g, 18.67 mmol) and quinolin-8-amine (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (7 g, 48.6 mmol) in DMF (124 mL) was stirred under nitrogen overnight at room temperature. The reaction mixture was diluted with saturated NaHCO3 (100 mL) and water (300 mL) yielding a yellow/brown precipitate which was filtered, washed with water (100 mL) and dried on high vacuum to obtain 4-iodo-N-(quinolin-8-yl)benzamide (9 g, 24.05 mmol, 64.4% yield) as a yellow brown solid. 1H NMR (400 MHz, DMSO-d6) δ=10.65 (s, 1H), 8.98 (dd, J=1.6, 4.3 Hz, 1H), 8.70 (dd, J=1.4, 7.6 Hz, 1H), 8.47 (dd, J=1.7, 8.3 Hz, 1H), 8.03-7.98 (m, 2H), 7.83-7.79 (m, 2H), 7.76 (dd, J=1.3, 8.2 Hz, 1H), 7.71-7.62 (m, 2H).

Provenance & Evidence