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0 °C

A flask was charged with compound 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline (5.5 g, 0.023 mol) and dichloromethane (50 mL). A solution of boron tribromide (27.6 mL, 1M solution in dichloromethane, 27.6 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes, then the cooling bath was removed and the reaction was stirred for 1.5 hours at room temperature. The reaction was quenched by slowly adding excess 10% aqueous hydrochloric acid, then the solution was basified to pH=6 with 20% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and filtered. Removal of the solvent gave 4 g of 5-(1-methyl-1H-pyrazol-4-yl)-quinolin-6-ol as a yellow solid.

1. customthe cooling bath was removed
2. stirringthe reaction was stirred for 1.5 hours at room temperature
3. customThe reaction was quenched by slowly adding excess 10% aqueous hydrochloric acid
4. extractionThe mixture was extracted with ethyl acetate
5. washthe organic phase was washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customRemoval of the solvent