Acetic Anhydride → N-(4,5-dimethylpyridin-2-yl)acetamide

HRID 1740954Notes

Reaction equation

HRID 1740954 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.NC1C(C)=C(C)C=CN=1.[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([CH3:25])=[CH:20][N:19]=1>>[C:5]([NH:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([CH3:25])=[CH:20][N:19]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 110078842-Amino-3,4-dimethylpyridineHCID 124040134,5-Dimethylpyridin-2-amine

Product 1

HCID 21834434N-(4,5-dimethylpyridin-2-yl)acetamide

Conditions

Temperature
137.5 °C

Procedure

Acetic anhydride (2.0 mL, 21 mmol) and 500 mg (4.09 mmol) of a 4:1 mixture of 2-amino-3,4-dimethylpyridine and 2-amino-4,5-dimethylpyridine (prepared by the method of W. O. Siegl, J. Heterocycl. Chem. 1981, 18, 1613-1618) were heated in a 135-140° C. oil bath for 2 h. The solution was concentrated on a rotary evaporator and the residue was chromatographed twice on silica gel, eluted with 30-50% ethyl acetate in dichloromethane to give 71 mg of pure 2-acetamido-4,5-dimethylpyridine.

Workup

  1. customprepared by the method of W
  2. concentrationThe solution was concentrated on a rotary evaporator
  3. customthe residue was chromatographed twice on silica gel
  4. washeluted with 30-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-03456bb030bb4b5496cb66e3186d8a19
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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