Ethanol → HCID 69506753, compound

HRID 2366668Notes

Reaction equation

HRID 2366668 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([O:24]CC)=[O:23])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4].C(O)C>O>[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]([CH3:27])([CH3:28])[C:22]([OH:24])=[O:23])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 69506730HCID 69506730, compound

Product 1

HCID 69506753HCID 69506753, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous sodium hydroxide (1.5 mL of 50%, 19 mmol) was added to a mixture of ethyl 3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropanoate (5.0 g, 14 mmol), ethanol (50 mL), and water (5 mL). The reaction was stirred for two hours at ambient temperature; an analysis by TLC indicated that starting material was present. Additional aqueous sodium hydroxide (0.5 mL of 50%) was added, and the reaction was heated at reflux for two hours and concentrated under reduced pressure. Ethanol (100 mL) was added to the residue and then removed under reduced pressure to provide 3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropanoic acid, which was dried overnight under vacuum.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours
  3. concentrationconcentrated under reduced pressure
  4. additionEthanol (100 mL) was added to the residue
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-c571358c36c14a87ac31404376fdf990
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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