m-Chloroperbenzoic acid → Methyl 2-methylnicotinate 1-oxide

HRID 2060609

Reaction equation

HRID 2060609 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>C(Cl)Cl>[CH3:1][C:2]1[N+:3]([O-:20])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 7015327Methyl 2-methylnicotinate

Product 1

HCID 20163965Methyl 2-methylnicotinate 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-methylpyridine-3-carboxylate (30 g, 198 mmol) was taken up in DCM (420 mL) and mCPBA (48.9 g, 218 mmol) was added. The resulting solution was stirred at room temperature overnight. The reaction mixture was purified directly by flash chromatography (silica, 0-20% MeOH/EtOAc) to afford the title compound as a beige solid. 1H NMR (500 MHz, d6-DMSO) δ 8.45 (d, 1H), 7.64 (d, 1H), 7.38 (t, 1H), 3.86 (s, 3H), 2.54 (s, 3H).

Workup

  1. customThe reaction mixture was purified directly by flash chromatography (silica, 0-20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-436bf10d20a14af4a037b2488e8b9794
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Linked notes

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