Acetic Anhydride → HCID 10330249, compound

HRID 1491823Notes

Reaction equation

HRID 1491823 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[CH:6]=[CH:5][CH:4]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:12]([O:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[CH:6]=[CH:5][CH:4]=1)(=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 149169816-(Hydroxymethyl)pyridine-2-carboxamide

Product 1

HCID 10330249HCID 10330249, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-hydroxymethyl-2-pyridinecarboxamide (80 g) and acetic anhydride (198.8 ml) in tetrahydrofuran (800 ml) was heated under reflux for 24 hours. The reaction mixture was added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated to give 6-acetoxymethyl-2-pyridinecarboxamide (93.34 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a41b5d5a4df04f98808c4599264e35b0
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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