Methyl bromoacetate → HCID 10617376, compound

Participants

Reaction Steps

A solution of 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.5 g) in DMF was stirred for 14 h with methyl bromoacetate (206 μl) and sodium bicarbonate (1.55 g). The reaction mixture was then partitioned between water and ethyl acetate. The aqueous phase was extracted with two further portions of ethyl acetate. The combined organic phases were washed with brine (3×), dried (MgSO4) and the solvent was removed in vacuo to give the crude product which was recrystallised from ethyl acetate-hexane to give the title compound, 208 mg; mp 188°-191° C. (ethyl acetate-hexanes); Found: C, 63.27; H, 4.24; N, 4.07. C18H14ClNO4 requires C, 62.89; H, 4.11; N, 4.07%; δ (360 MHz, DMSO-d6) 3.55 (3H, s, CO2CH3), 4.19 (2H, s, CH2CO2), 7.28 (1H, dd, J=2.6, 8.7 Hz, 6-H), 7.35-7.40 (6H, m, aromatics), 8.01 (1H, d, J=8.7 Hz, 5-H), 11.92 (1H, s, NH); m/z CI+ 344 (M+).

Provenance & Evidence