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 2383136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383136
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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 670510242-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-olAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a1ba77e82f5f4cab99bb6d45e434d688
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263594B2

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