8-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine → 2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol

HRID 2383136Notes

Reaction equation

HRID 2383136 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14](N)[C:13]3[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]([CH3:23])[C:12]=3[C:11]=2[CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:24]([C:21]1[N:22]([CH3:23])[C:12]2[C:11]3[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:20]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 575453008-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 670510242-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-olYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 8-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine (14.65 g, 42.4 mmol), prepared as described in Parts A-C of Example 59, in ethanol (1.2 L) was added to 10% palladium on carbon (6.77 g, 63.6 mmol) and a small amount of ethanol in a Parr vessel. The reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for 3.5 hours. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to a small volume. Hexanes were added, and the resulting mixture was allowed to stand overnight in a refrigerator. Crystals formed and were isolated by filtration, washed with hexanes (500 mL), and dried for three days under high vacuum to provide 9.40 g of 2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol as a white solid, mp 219-220.2° C.

Workup

  1. customfor 3.5 hours
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure to a small volume
  5. additionHexanes were added
  6. customCrystals formed
  7. customwere isolated by filtration
  8. washwashed with hexanes (500 mL)
  9. customdried for three days under high vacuum

Sources & evidence

ORD record
ord-a1ba77e82f5f4cab99bb6d45e434d688
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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