Ethanol → HCID 57446221, compound

HRID 1095356Notes

Reaction equation

HRID 1095356 reaction equation
Cl[C:2]1[C:11]2=[N:12][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]([CH3:15])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C([O-])=O.[NH4+].C(O)C>[Pd].C(#N)C>[CH3:15][C:14]1[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=[C:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:3]=[CH:2]2

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 57446220HCID 57446220, compound

Product 1

HCID 57446221HCID 57446221, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-1-methyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline (250 mg, 0.85 mmol) was combined with ammonium formate (268 mg, 4.25 mmol), ethanol (4 mL), and palladium on carbon (10%, 25 mg). The resulting gray suspension was warmed to 60° C. and stirred at this temperature for 18 hours. The reaction was cooled to ambient temperature and filtered through CELITE filter agent. The methanol was removed under reduced pressure and the resulting material was purified by automated flash chromatography (AnaLogix, eluted with a gradient of 0-30% CMA in chloroform) to provide material that was stirred in acetonitrile. A solid was isolated by filtration to provide 40 mg of 1-methyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline as a white powder, mp 128-130° C. MS (APCI) m/z 260 (M+H)+; Anal. calcd for C17H13N3.0.15H2O: C, 77.93; H, 5.12; N, 16.04. Found: C, 78.09; H, 5.51; N, 16.27.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationfiltered through CELITE
  3. filtrationfilter agent
  4. customThe methanol was removed under reduced pressure
  5. customthe resulting material was purified by automated flash chromatography (AnaLogix
  6. washeluted with a gradient of 0-30% CMA in chloroform)
  7. customto provide material that
  8. customA solid was isolated by filtration

Sources & evidence

ORD record
ord-0dea4ecc9e3e4c678c37bb293b51ed0c
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

Loading…