7-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline → 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2383173Notes

Reaction equation

HRID 2383173 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:20]([CH3:26])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:26][C:20]1[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[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

Participants

5

Reactant 2

HCID 670509187-benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1363405372-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-olYield 55.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Benzyloxy-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (16.11 g, 46.6 mmol), 10% palladium on carbon (4.96 g), and ethanol (380 mL) were combined. The mixture was shaken overnight under 50 psi (3.4×105 Pa) of hydrogen and then filtered. The solids were washed with ethyl acetate, and the filtrate was concentrated. Diethyl ether was added to the residue and a green solid formed. The solid was recrystallized from acetonitrile to give 6.63 g of 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol as a beige solid.

Workup

  1. filtrationfiltered
  2. washThe solids were washed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. additionDiethyl ether was added to the residue
  5. customa green solid formed
  6. customThe solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2c26dbf625c148a3bd799e625416eb06
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…