Sodium Hydroxide → 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 9381

Reaction equation

HRID 9381 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])=[C:9]([NH:14][C:15](=O)[CH2:16][O:17][CH2:18][CH3:19])[CH:10]=[N:11]2)=[CH:6][CH:5]=1>O.C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:21]([CH2:22][C:23]([CH3:25])([OH:26])[CH3:24])[C:15]([CH2:16][O:17][CH2:18][CH3:19])=[N:14][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21984424N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide

Product 1

HCID 219840281-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olYield 49.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (25 g, 0.625 mol) in water (205 mL) was added to a solution of N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide (170.88 g, 0.431 mol) in ethanol (700 mL), and the reaction was heated at reflux under a nitrogen atmosphere for two hours. Upon cooling the reaction, a precipitate formed and was isolated by filtration. The solid was purified by flash column chromatography on silica gel (eluting sequentially with chloroform, 99:1 chloroform:methanol, and 97:3 chloroform:methanol) to provide 80.31 g of 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a tan solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere for two hours
  3. temperatureUpon cooling
  4. customthe reaction
  5. customa precipitate formed
  6. customwas isolated by filtration
  7. customThe solid was purified by flash column chromatography on silica gel (
  8. washeluting sequentially with chloroform, 99:1 chloroform

Sources & evidence

ORD record
ord-2ad48777879c49898552a1d3c495787b
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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