Acetonitrile → 2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2203602Notes

Reaction equation

HRID 2203602 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:20]([CH2:29][CH3:30])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.C(#N)C>[Pd].CO>[CH2:29]([C:20]1[N:21]([CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=1)[CH3:30]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 670511697-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 1363318002-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-olYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-(Benzyloxy)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (8.3 g, 20.7 mmol) was added to a Parr vessel containing 10% palladium on carbon (1.5 g) wetted with acetonitrile. Methanol (160 mL) was added and the vessel was placed on the hydrogenator. The vessel was degassed three times and charged with 50 psi (3.4×105 Pa) hydrogen. The vessel was allowed to shake for 16 hours, replenishing the hydrogen as needed. The catalyst was removed by filtration through glass fiber filter paper. The catalyst was washed with 3:1 chloroform/methanol. The filtrates were combined. Evaporation under reduced pressure afforded 6.1 g of 2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-ol as a gray solid.

Workup

  1. customThe vessel was degassed three times
  2. additioncharged with 50 psi (3.4×105 Pa) hydrogen
  3. customThe catalyst was removed by filtration through glass fiber
  4. filtrationfilter paper
  5. washThe catalyst was washed with 3:1 chloroform/methanol
  6. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-31be526554324b559de1456f0bf11a77
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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