Acetic Anhydride → 4-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-one

HRID 1020557Notes

Reaction equation

HRID 1020557 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OC(=O)C)(=[O:22])C>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:22])[CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

Product 1

HCID 579504804-(4-(trifluoromethyl)benzyloxy)pyridin-2(1H)-oneYield 91%

Conditions

Temperature
80 °C

Procedure

4-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide (600 mg, 2.22 mmol) was heated to 140° C. in acetic anhydride (20 mL) for 2 h. The mixture was concentrated and then heated at 80° C. for 1 h in a mixture of MeOH (10 mL) and aqueous 1 N NaOH (10 mL). The resultant black solution was concentrated to a volume of 10 mL and extracted with CHCl3/EtOH (3:1). The organic layer was removed and concentrated to provide the title compound (550 mg, 91%) as a tan solid: 1H NMR (300 MHz, CD3OD) δ 7.70-7.60 (m, 4H), 7.41 (d, J=7.0 Hz, 1H), 6.17 (dd, J=7.0, 2.5 Hz, 1H), 5.96 (d, J=2.4 Hz, 1H), 5.18 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. concentrationThe resultant black solution was concentrated to a volume of 10 mL
  3. extractionextracted with CHCl3/EtOH (3:1)
  4. customThe organic layer was removed
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e703cccc112048c7a99bc3b51f3edf52
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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