Acetic Anhydride → 2-ACETAMIDO-6-METHYLPYRIDINE

HRID 451448Notes

Reaction equation

HRID 451448 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 157652-Amino-6-methylpyridine

Product 1

HCID 2204862-ACETAMIDO-6-METHYLPYRIDINE

Procedure

To a solution of 6-methyl-pyridin-2-ylamine (50 g, 0.462 mol) in acetic anhydride (200 mL) was heated to 90° C. for 90 minutes. The reaction mixture was cooled to room temperature and evaporated. An aqueous saturated solution of NaHCO3 was added to the residue until pH 8. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The title compound was obtained as a white solid (68 g, 98%).

Workup

  1. customevaporated
  2. additionAn aqueous saturated solution of NaHCO3 was added to the residue until pH 8
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-df255bac591b42d8b025e0a776322fc0
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…