Water → N-(4-(hydroxymethyl)pyridin-2-yl)acetamide

HRID 1984709Notes

Reaction equation

HRID 1984709 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:7]=1)(=O)C.[OH-].[Na+].O>O1CCCC1>[C:13]([NH:12][C:8]1[CH:7]=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][N:9]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 231508814-Acetoxymethyl-2-acetylaminopyridine

Product 1

HCID 23151114N-(4-(hydroxymethyl)pyridin-2-yl)acetamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Acetoxymethyl-2-acetylaminopyridine (Reference compound No. 11-1, 6.6 g, 32 mmol) was dissolved in tetrahydrofuran (20 mL), and 2N aqueous sodium hydroxide solution (19 mL, 38 mmol) was added dropwise thereto under ice-cooling. The mixture was stirred for 40 minutes at room temperature, and water (100 mL) was added thereto. The whole was extracted with ethyl acetate (80 mL) six times, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting solid was filtered off with the mixed solvent of ethyl acetate and hexane, and then the solid was dried under reduced pressure at 40° C. to give 4.5 g of the title reference compound as a colorless solid. (Yield 86%)

Workup

  1. temperatureunder ice-cooling
  2. extractionThe whole was extracted with ethyl acetate (80 mL) six times
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationthe resulting solid was filtered off with the mixed solvent of ethyl acetate and hexane
  6. customthe solid was dried under reduced pressure at 40° C.
  7. customto give 4.5 g of the title reference compound as a colorless solid

Sources & evidence

ORD record
ord-58ccb91b03064efaadb45e0d6d617f8a
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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