Pyridine → N-(4-methylpyridin-3-yl)acetamide

HRID 503857Notes

Reaction equation

HRID 503857 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].N1C=CC=CC=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>ClCCl>[C:15]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8])(=[O:17])[CH3:16]

Participants

5

Procedure

To solution of 3-amino-4-methylpyridine (540.2 Mg, 5.0 Mmol, 1 equiv) in dichloromethane (20 mL) was added pyridine (0.8 mL, 10.0 Mmol, 2 equiv) and acetic anhydride (0.57 mL, 6.0 Mmol, 1.2 equiv). The resultant solution was stirred at room temperature for 16 h and concentrated in vacuo to provide a crude residue. The residue was diluted with dichloromethane (200 mL), and washed with saturated sodium bicarbonate aqueous solution (50 mL) and brine (50 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to yield 3-acetylamino-4-methylpyridine (400.2 Mg) as yellow solid which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide a crude residue
  3. washwashed with saturated sodium bicarbonate aqueous solution (50 mL) and brine (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04cbf0a2d186487fbf29d8355421e0e3
Source dataset
uspto-grants-2010_08
Patent number
US07777035B2

Reaction notes

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