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0 °C

Ethyl (4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetate (0.500 g, 1.44 mmol) was dissolved in 15 mL of tetrahydrofuran and cooled to 0° C. Lithium aluminum hydride (55 mg, 1.44) was added. The mixture was allowed to stir overnight, slowly warming to ambient temperature. An additional 55 mg of lithium aluminum hydride was added, and the mixture was stirred for 24 hours at ambient temperature. 0.15 mL of water, followed by 0.15 mL of 2 N aqueous sodium hydroxide and 0.45 mL of water was added. After stirring at ambient temperature for 1 hour, the mixture was dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure. The residue was purified by automated flash chromatography eluting with a gradient of 0-50% CMA in chloroform. The residue was triturated with methanol, isolated by filtration and dried to provide 0.211 g of 1-(2-hydroxyethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a white solid, mp 310-312° C. MS (ESI) m/z 306 (M+H)+; Anal. calcd for C18H15N3O2: C, 70.81; H, 4.95; N, 13.76. Found: C, 70.52; H, 4.83; N, 13.66.

1. temperatureslowly warming to ambient temperature
2. stirringthe mixture was stirred for 24 hours at ambient temperature
3. additionwas added
4. stirringAfter stirring at ambient temperature for 1 hour
5. dry with materialthe mixture was dried over magnesium sulfate
6. filtrationfiltered through a layer of CELITE
7. filtrationfilter aid
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by automated flash chromatography
10. washeluting with a gradient of 0-50% CMA in chloroform
11. customThe residue was triturated with methanol
12. customisolated by filtration
13. customdried