Sodium Hydroxide → HCID 57447019, compound

HRID 2362525Notes

Reaction equation

HRID 2362525 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].[OH-].[Na+]>C(O)C.O>[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57447018HCID 57447018, compound

Product 1

HCID 57447019HCID 57447019, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate (39.0 g, 110 mmol) in ethanol (100 mL) was added a solution of sodium hydroxide (5.73 g, 143 mmol) in water (100 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure, the residue taken up in water (200 mL), the solution washed with dichloromethane (3×75 mL) and then acidified to about pH 6. The aqueous mixture was extracted with dichloromethane (3×75 mL), and then the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoic acid (31.0 g) as a solid that was used directly in the next step without further purification.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. washthe solution washed with dichloromethane (3×75 mL)
  3. extractionThe aqueous mixture was extracted with dichloromethane (3×75 mL)
  4. dry with materialthe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f00a5a28e154586a7d9e47ffaadde12
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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