m-Chloroperbenzoic acid → 2-Chloro-5-methoxy-3-methylpyridine 1-oxide

HRID 69314

Reaction equation

HRID 69314 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][CH3:21])=[CH:15][N:14]=1>ClCCl>[Cl:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([O:20][CH3:21])=[CH:15][N+:14]=1[O-:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128520162-Chloro-5-methoxy-3-methylpyridine

Product 1

HCID 867178152-Chloro-5-methoxy-3-methylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (70%, 695 mg, 2.82 mmol) was added to a solution of 2-chloro-5-methoxy-3-methylpyridine (370 mg, 2.35 mmol) in dichloromethane (10 mL). After stirring for 18 hours at room temperature, the reaction mixture was concentrated in vacuo and purified via silica gel chromatography (Gradient: 0% to 10% methanol in ethyl acetate) to afford the product as a white solid. Yield: 370 mg, 2.13 mmol, 91%. 1H NMR (400 MHz, CD3OD) δ 8.14 (d, J=2.5 Hz, 1H), 7.23 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 2.44 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified via silica gel chromatography (Gradient: 0% to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-04113bd597ee43be87c8b0ace7ac50f1
Source dataset
uspto-grants-2014_09
Patent number
US08822494B2

Linked notes

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