Acetic Anhydride → 4-Acetoxymethyl-2-acetylaminopyridine

HRID 1984708Notes

Reaction equation

HRID 1984708 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].[C:17](OCC)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:10]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:17](=[O:19])[CH3:18])[CH:7]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 1515296(2-Aminopyridin-4-yl)methanol

Product 1

HCID 231508814-Acetoxymethyl-2-acetylaminopyridineYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2-Aminopyridin-4-yl)methanol (5.0 g, 40 mmol) was suspended in pyridine (20 mL), acetic anhydride (11 mL, 120 mmol) was added thereto under ice-cooling, and the mixture was stirred for 5 hours at room temperature. Ethyl acetate (150 mL) was added to the reaction mixture, and then the mixture was washed with water (150 mL), saturated aqueous sodium hydrogen carbonate solution (150 mL) and brine (150 mL) successively. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting solid was filtered off with hexane, then dried under reduced pressure at 40° C. to give 6.7 g of the title reference compound as a colorless solid. (Yield 79%)

Workup

  1. temperatureunder ice-cooling
  2. washthe mixture was washed with water (150 mL), saturated aqueous sodium hydrogen carbonate solution (150 mL) and brine (150 mL) successively
  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 hexane
  6. customdried under reduced pressure at 40° C.
  7. customto give 6.7 g of the title reference compound as a colorless solid

Sources & evidence

ORD record
ord-42b1ae3ce27a476fa4d680073751548c
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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