Methanol, 1,1-diethoxy-, 1-acetate → 7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline

HRID 2383102Notes

Reaction equation

HRID 2383102 reaction equation
[C:1](OC(OCC)OCC)(=O)C.[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([NH:31][CH2:32][CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:25]([NH2:30])[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:31]([CH2:32][CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:1]=[N:30][C:25]=3[CH:26]=[N:27][C:28]=2[CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine

Product 1

HCID 670509547-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolineYield 101.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, diethoxymethyl acetate (3.0 mL, 18 mmol) was added dropwise to a solution of 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine (3.0 g, 7.8 mmol) in toluene (30 mL), and the reaction was heated at reflux for three hours. The reaction mixture was concentrated under reduced pressure until a small volume of solvent remained. Hexanes were added, and the resulting mixture was cooled for 20 minutes in a refrigerator. A precipitate formed which was isolated by filtration, washed with hexanes, and dried overnight under reduced pressure to provide 3.12 g of 7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline as a solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for three hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure until a small volume of solvent
  4. additionHexanes were added
  5. temperaturethe resulting mixture was cooled for 20 minutes in a refrigerator
  6. customA precipitate formed which
  7. customwas isolated by filtration
  8. washwashed with hexanes
  9. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-f3934dee5d374b6bac83d6ba052decaa
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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