Sodium Hydroxide → HCID 57447027, compound

HRID 2366612Notes

Reaction equation

HRID 2366612 reaction equation
[OH-].[Na+].[N:3]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1>O.C(O)C>[N:3]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57447025HCID 57447025, compound

Product 1

HCID 57447027HCID 57447027, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (1.66 g, 41.7 mmol) in water (15 mL) was added to a solution of ethyl 6-(1H-imidazo[4,5-c]quinolin-1-yl)hexanoate (10.0 g, 32.1 mmol, prepared in Part A of Example 10) in ethanol (75 mL), and the reaction was stirred at ambient temperature for two hours and then concentrated under reduced pressure. The residue was diluted with water and adjusted to pH 5 with the addition of 10% hydrochloric acid. The mixture was extracted with dichloromethane, and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.5 g of 6-(1H-imidazo[4,5-c]quinolin-1-yl)hexanoic acid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. additionadjusted to pH 5 with the addition of 10% hydrochloric acid
  4. extractionThe mixture was extracted with dichloromethane
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c669fdcb08da45938f39fb832344fddc
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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