m-Chloroperbenzoic acid → HCID 23088707, compound

HRID 2109053Notes

Reaction equation

HRID 2109053 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>ClCCl>[OH:1][C:2]1[CH:7]=[N+:6]([O-:20])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 23088707HCID 23088707, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 5-hydroxypyridin-2-carboxylate (5.30 g) in dichloromethane (75 ml), m-chloroperbenzoic acid (>65%, 11.0 g) is added under ice-cooling, and the mixture is stirred at room temperature for 5 hours. The reaction solution is concentrated under reduced pressure. The residue is suspended in ethyl acetate and collected by filtration to give the title compound (4.62 g). Mother liquor is concentrated under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent: chloroform to methanol/chloroform=1/5). The resulting solid is suspended in ethyl acetate/diethyl ether and collected by filtration to give the title compound (0.68 g).

Workup

  1. additionis added under ice-
  2. temperaturecooling
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c1de0ec003524ee1b45dcd384bb4a309
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Reaction notes

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