Sodium Hydroxide → HCID 69506718, compound

HRID 2366743Notes

Reaction equation

HRID 2366743 reaction equation
[OH-].[Na+].Cl.[CH2:4]([O:6][CH2:7][C:8]([NH:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[NH:21][CH2:22][C:23]1([C:29]([O:31]CC)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH3:5]>C(O)C.O>[CH2:4]([O:6][CH2:7][C:8]1[N:21]([CH2:22][C:23]2([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=1)[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69506831HCID 69506831, compound

Product 1

HCID 69506718HCID 69506718, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Sodium hydroxide (2.71 g, 67.7 mmol) was added to a solution of ethyl 1-[({3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)methyl]cyclohexanecarboxylate hydrochloride (10.15 g, 22.6 mmol) in 9:1 ethanol/water (30 mL), and the solution was heated at reflux for several hours. The ethanol was removed under reduced pressure, and the resulting solution was diluted with water and adjusted to pH 4 to 5 with the addition of 3 M hydrochloric acid. The mixture was then extracted several times with dichloromethane The aqueous fraction was adjusted to pH 7 and extracted several more times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 5.73 g of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxylic acid.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for several hours
  3. customThe ethanol was removed under reduced pressure
  4. additionthe resulting solution was diluted with water
  5. additionadjusted to pH 4 to 5 with the addition of 3 M hydrochloric acid
  6. extractionThe mixture was then extracted several times with dichloromethane The aqueous fraction
  7. extractionextracted several more times with dichloromethane
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56689984555e4b3e8e346f5d266b4fcd
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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