Ammonium formate → 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2203499Notes

Reaction equation

HRID 2203499 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]([CH2:26][CH2:27][CH3:28])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:24][CH:23]([CH3:25])[CH2:22][N:21]1[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]=[C:20]1[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 670509177-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 1363405361-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-olYield 56.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

7-Benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline (60.3 g, 0.188 mol), prepared as described in Parts A-G of Example 1, and 10% palladium on carbon (10 g) were mixed with ethanol (500 mL). Ammonium formate (101.53 g, 1.61 mol) and ethanol (500 mL) were then added, and the reaction mixture was heated at reflux for two hours. The mixture was allowed to cool to ambient temperature slowly and stirred overnight. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with ethanol (1 L), methanol (2 L) and dichloromethane (2 L). The combined filtrates were concentrated under reduced pressure to provide a tan solid, which was triturated with cold ethanol and isolated by filtration to yield 30 g of 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol as a tan, granular solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for two hours
  3. filtrationThe reaction mixture was filtered through a layer of CELITE
  4. filtrationfilter aid
  5. washthe filter cake was washed with ethanol (1 L), methanol (2 L) and dichloromethane (2 L)
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. customto provide a tan solid, which
  8. customwas triturated with cold ethanol
  9. customisolated by filtration

Sources & evidence

ORD record
ord-5b118608f774442aad7d1ea0a9d5d70c
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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