m-Chloroperbenzoic acid → 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester N-oxide

HRID 251598Notes

Reaction equation

HRID 251598 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:6][CH:5]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N+:6]([O-:28])[CH:5]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 596783286-(2,6-Diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

Product 1

HCID 669936046-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester N-oxide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester (2.1 g, 7.1 mmol) and 3-chloroperoxybenzoic acid (77%, 1.9 g) in CH2Cl2 (50 mL) is stirred at room temperature overnight. The mixture is diluted with ether (600 mL) and washed with saturated Na2CO35 then brine, and dried. Concentration at reduced pressure gives 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester N-oxide. 1H NMR (CDCl3) 8.89 (s, 1H), 7.26 (t, 1H), 7.19 (m, 3H), 3.95 (s, 3H), 3.02 (q, 2H), 2.04 (m, 2H), 2.30 (m, 2H), 1.26 (t, 3H), 1.11 (t, 6H).

Workup

  1. washwashed with saturated Na2CO35 then brine
  2. customdried
  3. concentrationConcentration at reduced pressure

Sources & evidence

ORD record
ord-5857651ae45c4098aba0df174ca86cae
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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