Water → 1-(2-hydroxyethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095363Notes

Reaction equation

HRID 1095363 reaction equation
[O:1]=[C:2]1[C:11]2=[N:12][N:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:14]([CH2:15][C:16](OCC)=[O:17])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:17][CH2:16][CH2:15][C:14]1[N:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:3][C:2]2=[O:1]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 57612919Ethyl (4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetate

Product 1

HCID 574462281-(2-hydroxyethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-oneYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5405a23afe5f4fccacea6e728cfa5d57
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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