Dimethylformamide → 2-Acetoxy-8-(2-oxopropoxy)quinoline

Participants

Reaction Steps

A mixture of 5b (1.02 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) was stirred at room temperature for 30 min and then chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) was added in one portion. The resulting mixture was continued to stir at room temperature for 24 h (monitored by TLC). After this period, it was poured into ice water (100 ml) and the pale yellow solid thus obtained was crystallized from dichloromethane and ether to afford 2-Acetoxy-8-(2-oxopropoxy)quinoline (5c) (0.85 g, 66%). mp: 79°-80° C.; 1H-NMR (CDCl3): δ2.16 (s, 3H, OAc), 2.42 (s, 3H, 3'-CH3), 4.85 (s, 2H, OCH2), 7.06 (d, 3-H), 7.26-7.67 (m, 3H, Ar--H), 8.08 (d, 4-H).

Provenance & Evidence