Imidazole → 6-(1H-imidazol-1-yl)-2-methoxy-quinoline

Participants

Reaction Conditions

Reaction Steps

6-bromo-2-methoxy-quinoline (19 g; 79.8 mmol; RN: 99455-05-7) was dissolved in dry DMF (100 mL), imidazole (5.7 g; 84 mmol), K2CO3 (11.6 g, 84 mmol), and CuI (1.1 g, 4.2 mmol) were added at r.t. under stirring and in argon atmosphere. The resulting mixture was heated at 150° C. for 48 hours. The reaction mixture was cooled at r.t. and poured into 2% (w/w) aqueous EDTA solution (600 mL), the resulting precipitate was filtered and washed with water, dried and then suspended in hexane/AcOEt. The resulting suspension was stirred for 10 min., filtered and the collected title product was dried, 14 g (yield 78%) of white crystals were obtained. C13H11N3O, MW: 225.25. MS (ESI) m/z: 226 (M+1). 1H-NMR (200 MHz, CDCl3) ppm: 3.6 (s, 3H), 6.97 (s, 1H), 7.51 (s, 1H), 7.82 (d, 1H), 8.10 (dd, 1H), 8.13 (d, 1H), 8.27 (s, 1H), 8.84 (d, 1H).

Provenance & Evidence