7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline → 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 2203560Notes

Reaction equation

HRID 2203560 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]4[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]4)[C:20]([CH2:30][O:31][CH2:32][CH3:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C(#N)C.C(Cl)(Cl)Cl.CO.[OH-].[Pd+2].[OH-]>[CH3:28][C:25]1([CH3:29])[O:24][CH:23]([CH2:22][N:21]2[C:13]3[C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=4[N:16]=[CH:15][C:14]=3[N:19]=[C:20]2[CH2:30][O:31][CH2:32][CH3:33])[CH2:27][O:26]1

Participants

5

Reactant 1

HCID 670511477-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 1363478501-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-olYield 93.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6342AcetonitrileSolventHCID 21584188Chloroform methanolSolvent

Procedure

Palladium hydroxide (Pearlman's catalyst) (20% wt. % palladium on carbon, 2.2 g) was added to a solution of 7-benzyloxy-1-[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (22.2 g, 49.6 mmol) in acetonitrile (400 mL) and the reaction mixture was hydrogenated (30 psi, 2.1×105 Pa) for 24 hours on a Parr apparatus. The crude reaction mixture was diluted with 1:1 chloroform/methanol (1 L), then was filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and triturated with acetonitrile. The resulting crystalline material was collected by filtration, washed with acetonitrile, and dried to afford 16.55 g of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-7-ol as a white powder, mp 239-240° C.

Workup

  1. customfor 24 hours
  2. customThe crude reaction mixture
  3. filtrationwas filtered through a layer of CELITE filter agent
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customtriturated with acetonitrile
  6. filtrationThe resulting crystalline material was collected by filtration
  7. washwashed with acetonitrile
  8. customdried

Sources & evidence

ORD record
ord-5b15182092a640f1b7250dacd040ea9a
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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