m-Chloroperbenzoic acid → 2-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

HRID 2060611Notes

Reaction equation

HRID 2060611 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:21]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19081344Methyl 2-(chloromethyl)pyridine-3-carboxylate

Product 1

HCID 582166522-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(chloromethyl)pyridine-3-carboxylate (20.73 g, 112 mmol) was taken up in dichloromethane (225 mL) and mCPBA (27.5 g, 123 mmol) was added. The resulting solution was stirred at room temperature overnight. Saturated aqueous sodium bicarbonate was added and the products extracted into dichloromethane (2×). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography (silica, 0-20% methanol/ethyl acetate) gave the title compound as a white solid. 1H NMR (d6-DMSO, 600 MHz) δ 8.50 (dd, 1H), 7.75 (dd, 1H), 7.53 (dd, 1H), 5.07 (s, 2H), 3.86 (s, 3H).

Workup

  1. extractionthe products extracted into dichloromethane (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography (silica, 0-20% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-43256acf3b6e4a4b98386744e22d2a6a
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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