Hydrochloric Acid → HCID 14722778, compound

Participants

Reaction Steps

To a solution of n-BuLi (28 mL, 44.0 mmol, 1.6M in hexanes) at −78° C. was added a solution of 8-bromoquinoline (8.5 g, 40.0 mmol) in Et2O (60 mL) over 20 minutes. After stirring for 22 minutes, a solution of 2-chloro-N-methoxy-N-methylacetamide (5.7 g, 41 mmol) in THF (35 mL) was added over 12 minutes (see Tillyer, R. et al; Synlett 225-226, 1996; and Dolling, U. H. et al; U.S. Pat. No. 5,786,515). After 3 hours the reaction was poured into 11 mL, 4N HCl. The aqueous phase was neutralized to pH 7 using solid NaHCO3 and partitioned with Et2O (2×100 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. Purification via SiO2 chromatography (20% EtOAc/hexanes) afforded the product as a yellow solid (4.2 g). 1H NMR (300 Hz, CDCl3) δ 9.0-8.96 (m, 1H), 8.26-8.19 (m, 2H), 8.04-8.01 (m, 1H), 7.68-7.63 (m, 1H), 7.52-7.48 (m, 1H), 5.37 (s, 2H).

Provenance & Evidence