Sodium Hydroxide → 5,6-Dihydro-8-methoxy-2-(quinolin-2-ylmethylthio)-4H-imidazo-[4,5,1-ij]quinoline

Participants

Reaction Steps

2-Chloromethylquinoline hydrochloride (0.845 g, 4.0 mmol) was added to a solution of 5,6-dihydro-8-methoxy-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione (0.871 g, 4.0 mmol) in 1 N-NaOH (8 ml) and EtOH (8 ml). The mixture was heated to reflux, cooled to room temperature, concentrated in vacuo, and the aqueous residue extracted with CH2Cl2 (50 ml). The extract was washed with 1NNaOH (2×30 ml), and brine (20 ml), dried (MgSO4), and evaporated in vacuo to give an oil which was purified by chromatography (SiO2, Et2O) and trituration with Et2O-petrol ether to give the title compound (0.885 g, 62%) as yellow crystals, mp 89°-91° C. (Found: C,70.1; H,5.4; N,11.4; C21H19N3OS requires C,69.8; H,5.3; N,11.6%).

Provenance & Evidence