反应详情

2-Methyl-8-hydroxyquinoline (0.80 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) were stirred at room temperature for 30 min. To this solution was added chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) in one portion. The resulting mixture was stirred at room temperature for 24 h. (monitored by TLC) and then poured into ice water (100 ml). The pale yellow solid thus obtained was collected and crystallized from dichloromethane and ether to afford 2-methyl-8-(2-oxopropoxy)quinoline (10a) (0.77 g, 72%). mp: 99°-100° C.; 1H-NMR (CDCl3): δ2.35 (s, 3H, 2'-CH3), 2.79 (s, 3H, 2-CH3), 4.86 (s, 2H, OCH2), 6.88-7.44 (m, 3H, Ar--H), 7.33 (d, 1H, 3-H), 8.03 (d, 1H, 4-H).

1. customThe pale yellow solid thus obtained
2. customwas collected
3. customcrystallized from dichloromethane and ether