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

HRID 521331Notes

Reaction equation

HRID 521331 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). The reaction mixture was stirred at room temperature overnight, then the ethanol was removed under reduced pressure. The remaining aqueous solution was washed with dichloromethane and adjusted to pH 5 with 10% aqueous hydrochloric acid. The aqueous layer was extracted with dichloromethane (2×). The later organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to yield 11.5 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid as yellow solid.

Workup

  1. customthe ethanol was removed under reduced pressure
  2. washThe remaining aqueous solution was washed with dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane (2×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81be424208d1476c8428b4d37e632dea
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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