Potassium Carbonate → alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

HRID 547331Notes

Reaction equation

HRID 547331 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[OH:8][C:9]([CH3:29])([CH3:28])[CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:22][C:23](=O)[CH2:24][O:25][CH3:26]>O.C(O)C.[Cl-].[Na+].O>[CH3:26][O:25][CH2:24][C:23]1[N:11]([CH2:10][C:9]([CH3:29])([OH:8])[CH3:28])[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 67204879N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride

Product 1

HCID 15224447alpha,alpha-Dimethyl-2-methoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanolYield 90.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of potassium carbonate (3.4 g, 24.3 mmol) in water (9 mL) was added to a stirred suspension of N-{4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-methoxyacetamide hydrochloride (5.5 g, 16.2 mmol) in ethanol (23 mL). The reaction mixture was heated at reflux for 1.5 hours, then was allowed to cool to room temperature. The mixture was concentrated under reduced pressure to yield an aqueous slurry that was diluted with water (50 mL) and a small amount of brine. The mixture was extracted with dichloromethane (2×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude oil was purified by flash chromatography (silica gel, 5% methanol in dichloromethane) to yield 4.2 g of 1-[2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an oil that slowly solidified.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto yield an aqueous slurry that
  5. extractionThe mixture was extracted with dichloromethane (2×50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude oil was purified by flash chromatography (silica gel, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c20867ceaed54832b3c5f76ae567ffbb
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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