8-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline → 2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol
Reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:20]([CH2:25][O:26][CH2:27][CH3:28])[N:21]([CH2:22][CH2:23][CH3:24])[C:12]=3[C:11]=2[CH:10]=1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:27]([O:26][CH2:25][C:20]1[N:21]([CH2:22][CH2:23][CH3:24])[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:19]=1)[CH3:28]Participants
Procedure
8-Benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline (15.00 g, 39.84 mmol) and ethanol (300 mL) were added to a Parr vessel. A mixture of palladium hydroxide (2.0 g, 20% on carbon) in ethanol (100 mL) was then added. The vessel was purged with nitrogen, placed under hydrogen pressure (25 psi, 1.7×105), and shaken for three hours. The vessel was then refilled with hydrogen (25 psi, 1.7×105) and shaken for 18 hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol (2 L). The filtrate was concentrated under reduced pressure, and the resulting orange oil was dissolved in toluene and concentrated under reduced pressure to provide 10.7 g of 2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol as a granular, orange solid.
Workup
- additionwas then added
- customThe vessel was purged with nitrogen
- additionThe vessel was then refilled with hydrogen (25 psi, 1.7×105)
- stirringshaken for 18 hours
- filtrationThe reaction mixture was filtered through a layer of CELITE
- filtrationfilter aid
- washthe filter cake was washed with methanol (2 L)
- concentrationThe filtrate was concentrated under reduced pressure
- dissolutionthe resulting orange oil was dissolved in toluene
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6e659a430f7f4c52a0ebaa6d96d6c2ed
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365567B2
Reaction notes
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