Toluene → 4-tert-Butyl-N-(2-chloro-quinolin-3-yl)-benzamide

Participants

Reaction Steps

A solution of trimethylaluminum in toluene (2.0 M, 0.56 mL, 1.12 mmol) was added to a solution of 2-chloro-quinolin-3-ylamine (0.2 g, 1.12 mmol) and methyl 4-tert-butylbenzoate (0.227 mL, 1.18 mmol) in 1,2-dichloroethane (10 mL). The solution was heated at reflux for 6 hours, cooled to room temperature and treated with methanol (˜1 mL). The product was preabsorbed onto silica gel, and purified by flash chromatography, using 10% ethyl acetate in hexane as the eluant to give the product as a colorless solid, 0.32 g (84%). MS: m/z 339 (MH+). 1H NMR (DMSO-d6): δ 1.34 (s, 9 H), 7.60 (d, 2 H), 7.69 (d of d, 1 H), 7.82 (d of d, 1 H), 7.99 (d, 3 H), 8.09 (d, 1 H), 8.67 (s, 1 H) and 10.31 (s, 1 H).

Provenance & Evidence