Ethanol → HCID 67457278, compound

HRID 2389291Notes

Reaction equation

HRID 2389291 reaction equation
[C:1]([C:5]1[N:6]([CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:7]=[C:8]([C:10]2[CH:11]=C([CH:15]=[CH:16][CH:17]=2)C#N)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>>[C:1]([C:5]1[N:6]([CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:7]=[C:8]([C:10]2[CH:11]=[C:28]([CH:15]=[CH:16][CH:17]=2)[C:27]([OH:25])=[O:29])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24936395HCID 24936395, compound

Product 1

HCID 67457278HCID 67457278, compoundYield 98%

Procedure

Compound 1 (0.17 g, 0.53 mmol) obtained in Example 1 was dissolved in ethanol (60 mL), and a 2 mol/L aqueous sodium hydroxide solution (60 mL, 120 mmol) was added thereto, and then, the mixture was refluxed overnight. After the mixture was left to cool to room temperature, the solvent was evaporated under reduced pressure. To the residue, 2 mol/L hydrochloric acid was added to adjust the pH of the mixture to 4. Then, the mixture was extracted with chloroform, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure to give the title compound a (178 mg, 0.52 mmol, yield: 98%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. waitAfter the mixture was left
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the residue, 2 mol/L hydrochloric acid was added
  5. extractionThen, the mixture was extracted with chloroform
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5b051f04f21d42fd931e90adcd0e995e
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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