1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-ol

HRID 2105486Notes

Reaction equation

HRID 2105486 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[CH2:23][CH2:24][CH3:25])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[NH2:22][C:13]1[C:12]2[N:11]=[C:10]([CH2:23][CH2:24][CH3:25])[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

5

Reactant 2

HCID 575388311-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 575388154-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.2 g, 9.6 mmol) and 10% palladium on carbon (0.15 g) in ethanol (125 mL) was placed under hydrogen pressure (30 psi, 2.1×105 Pa) and shaken on a Parr apparatus for 80 minutes. After 40 minutes the hydrogen pressure had decreased to 20 psi, (14×105 Pa). The reaction mixture was filtered through a layer of CELITE filter agent, and the filtrate was concentrated under reduced pressure. The residue (2.4 g) was recrystallized three times from methanol/water and dried overnight in a vacuum oven at 70° C. to provide 4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-ol as white crystals, mp 232-235° C.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue (2.4 g) was recrystallized three times from methanol/water
  4. customdried overnight in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-402bf239cb744450be90da71509c35ed
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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