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

HRID 1392630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392630
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 (60 mL) and washed with saturated Na2CO3, 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).

Aufarbeitung

  1. washwashed with saturated Na2CO3
  2. dry with materialbrine, and dried
  3. concentrationConcentration at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8e92bd9f81e6466cbfc168a6eb3a1173
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342115B2

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