Acetic Anhydride → 4-(Pyridin-2-ylmethoxy)pyridin-2(1H)-one

HRID 2387513Notes

Reaction equation

HRID 2387513 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=1.C(OC(=O)C)(=[O:18])C>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:18])[CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 684584404-(Pyridin-2-ylmethoxy)pyridine 1-oxide

Product 1

HCID 579502834-(Pyridin-2-ylmethoxy)pyridin-2(1H)-oneYield 21%

Conditions

Temperature
80 °C

Procedure

4-(Pyridin-2-ylmethoxy)pyridine 1-oxide (9.0 g, 45 mmol) was heated at 140° C. in acetic anhydride (100 mL) for 2 h. The solution was concentrated and then heated at 80° C. for 1 h in a mixture of MeOH (50 mL) and H2O (50 mL). The resultant black solution was concentrated and the residue was dissolved in hot i-PrOH (40 ml). Et2O (250 mL) was added and the mixture was placed in the freezer for 16 h. The solid was filtered off to provide the title compound (19 g, 21%) as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 11.13 (br s, 1H), 8.58 (d, J=4.7 Hz, 1H), 7.88-7.81 (dt, J=7.9, 1.6 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.38-7.34 (m, 1H), 7.26 (d, J=7.3 Hz, 1H), 5.96-5.95 (dd, J=7.3, 2.5 Hz, 1H), 5.76 (d, J=3.4 Hz, 1H), 5.12 (s, 2H).

Workup

  1. concentrationThe solution was concentrated
  2. concentrationThe resultant black solution was concentrated
  3. dissolutionthe residue was dissolved in hot i-PrOH (40 ml)
  4. additionEt2O (250 mL) was added
  5. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-16b592ba04a34150aa9eac22ba0e3ebf
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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