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

HRID 1095363노트

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HRID 1095363 반응식
[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]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2회HCID 57612919Ethyl (4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5405a23afe5f4fccacea6e728cfa5d57
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138173B2

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