Acetic Anhydride → 3-(4-Nitrophenyl)pyridin-2(1H)-one

HRID 2218116Notes

Reaction equation

HRID 2218116 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N+:12]([O-])[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(OC(=O)C)(=[O:19])C>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:19])[NH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 45557493-(4-Nitrophenyl)pyridine-1-oxide

Product 1

HCID 541614103-(4-Nitrophenyl)pyridin-2(1H)-one

Procedure

3-(4-Nitrophenyl)pyridine-1-oxide (P2, 2.5 g, 11.6 mmol) was stirred at reflux in acetic anhydride (25 mL) for 18 hours, then allowed to cool. The reaction mixture was concentrated and concentrated hydrochloric acid (25 mL) was added. The solution was stirred at reflux for 4 hours, then allowed to cool. The reaction mixture was poured onto ice/water and filtration followed by drying under high vacuum afforded the title compound as a solid.

Workup

  1. temperatureto cool
  2. concentrationThe reaction mixture was concentrated
  3. additionconcentrated hydrochloric acid (25 mL) was added
  4. temperatureat reflux for 4 hours
  5. temperatureto cool
  6. additionThe reaction mixture was poured onto ice/water and filtration
  7. customby drying under high vacuum

Sources & evidence

ORD record
ord-b7d47c247a274c1ba22d9494a23fd9e0
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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