Water → HCID 22142213, compound

Participants

Reaction Steps

To a light brown solution of 8-bromo-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester (Reference Example 24c) (4.98 g, 11.3 mmol) in 75 mL 3:1:1 tetrahydrofuran:methanol:water was added lithium hydroxide monohydrate (1.367 g, 32.6 mmol). The reaction was stirred at room temperature for 5 hours. The reaction mixture was concentrated and then poured into water. The solution was acidified to pH 2 with 1 N HCl and the resulting solids were isolated by filtration. The solids were then suspended in methanol and filtered to afford the desired product (2.6732 g, 80%). An additional 0.5768 g (17%) of product was obtained from the methanol filtrates. 1H NMR (300 MHz, DMSO, d6, TFA Shake) δ 7.86 (d, 1 H, Jm=2.7 Hz, ArH5), 7.55 (d, 1 H, Jm=2.7 Hz, ArH7), 7.32 (s, 1 H, C═CH), 3.94 (s, 3 H, OCH3); Mass Spec.: calc. for [C11H8BrNO4+H]+ Theor. m/z=298, 300; Obs.=298, 300.

Provenance & Evidence