Ethyl Acetate → 5-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 2370867Notes

Reaction equation

HRID 2370867 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:15].CCOC(C)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N+:7]([O-:15])[CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 133587775-Methoxy-2-methylpyridine

Product 1

HCID 122140195-Methoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methoxy-2-methylpyridine (15 g, 0.121 mol) in DCM (200 mL) was added 3-chloro peroxybenzoic acid (23.14 g, 0.134 mol, Aldrich). The reaction was stirred at rt for 3 h. Reaction progress was monitored by TLC (50% EtOAc in petroleum ether). After completion of reaction, the reaction mixture was concentrated under reduced pressure providing the product as a yellow oil. The oil was dissolved in EtOAc (50 mL) and passed through a silica gel plug (60-120 mesh) and the plug eluted with 10% MeOH in CHCl3 to give the title compound as a colorless liquid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (d, J=2.4 Hz, 1H), 7.37 (d, J=8.7 Hz, 1H), 6.98 (dd, J=2.7 and 8.7 Hz, 1H), 3.78 (s, 3H), 2.26 (s, 3H). MS (ESI, positive ion) m/z: 140.0 (M+H).

Workup

  1. customReaction progress
  2. customAfter completion of reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f0ec2f88286b4a74926c46130da746ef
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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