HCID 57538830, compound → HCID 57538840, compound

HRID 2105476Notes

Reaction equation

HRID 2105476 reaction equation
C([O:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:22])[C:12]=2[N:11]=[C:10]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C1C=CC=CC=1>[Pd].C(O)C>[NH2:22][C:13]1[C:12]2[N:11]=[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:9]([OH:8])[C:21]=2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

4

Reactant 1

HCID 57538830HCID 57538830, compound

Product 1

HCID 57538840HCID 57538840, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(benzyloxy)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine (0.32 g, 0.87 mmol) and 10% palladium on carbon (0.015 g) in ethanol (10 mL) was placed in a pressure vessel, which was purged with hydrogen three times and then placed under hydrogen pressure (45 psi, 3.1×105 Pa) and shaken on a Parr apparatus for 18 hours. An analysis by LC/MS indicated the presence of starting material. Additional 10% palladium on carbon (0.05 g) was added, and the hydrogenation was continued for an additional five hours. The reaction mixture was filtered, and the filter cake was washed with ethanol. After several days, crystals formed in the filtrate. The filtrate was concentrated under reduced pressure until it became cloudy, and the mixture was allowed to stand for 18 hours. More crystals formed, and the crystals were collected by filtration, washed with diethyl ether, and dried to provide 0.068 g of 4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-ol as an off-white powder, decomp. 201-209° C.

Workup

  1. customwas placed in a pressure vessel
  2. customwhich was purged with hydrogen three times
  3. additionAdditional 10% palladium on carbon (0.05 g) was added
  4. waitthe hydrogenation was continued for an additional five hours
  5. filtrationThe reaction mixture was filtered
  6. washthe filter cake was washed with ethanol
  7. waitAfter several days
  8. customcrystals formed in the filtrate
  9. concentrationThe filtrate was concentrated under reduced pressure until it
  10. waitto stand for 18 hours
  11. customMore crystals formed
  12. filtrationthe crystals were collected by filtration
  13. washwashed with diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-0af8edcd7a3544ec85270c748adde573
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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