Sodium Hydroxide → 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid

HRID 2366682Notes

Reaction equation

HRID 2366682 reaction equation
[OH-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[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]=1)[CH2:4][CH3:5]>O.C(O)C>[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[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]=1)[CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57447069ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate

Product 1

HCID 574470705-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acidYield 85.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (2.23 g, 55.9 mmol) in water (100 mL) was added to a solution of ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (14.6 g, 43.0 mmol) in ethanol (100 mL), and the reaction was stirred at ambient temperature overnight, concentrated to remove ethanol, and washed with dichloromethane. The resulting solution was adjusted to pH 5 with the addition of 10% hydrochloric acid. The mixture was extracted twice with chloroform, and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 11.5 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid.

Workup

  1. concentrationconcentrated
  2. customto remove ethanol
  3. washwashed with dichloromethane
  4. additionThe resulting solution was adjusted to pH 5 with the addition of 10% hydrochloric acid
  5. extractionThe mixture was extracted twice with chloroform
  6. dry with materialthe combined extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd7fa5a239c644d9a116f34f06efda45
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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