Water → 1-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinoline

HRID 599453Notes

Reaction equation

HRID 599453 reaction equation
O.[OH-].[Na+].[CH3:4][CH:5]([CH3:29])[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:18][C:19](=O)[CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1>C(O)C>[CH3:4][CH:5]([CH3:29])[CH2:6][N:7]1[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=[C:19]1[CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67052427N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide

Product 1

HCID 670523821-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinolineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Water (3 mL) followed by solid sodium hydroxide (0.4 g, 10.7 mmol) were added to a stirred solution of N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide (2.55 g, 7.13 mmol) in ethanol (10 mL). The reaction mixture was heated at reflux for 30 minutes, then was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting aqueous slurry was diluted with water (50 mL) and was extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 2.3 g of crude 1-(2-methylpropyl)-2-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1H-imidazo[4,5-c]quinoline as a clear oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 30 minutes
  3. concentrationwas concentrated under reduced pressure
  4. additionThe resulting aqueous slurry was diluted with water (50 mL)
  5. extractionwas extracted with dichloromethane (2×50 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a122de7f1634d819c95b57edaab530c
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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