Trifluoroacetic anhydride → 2,6-dichloro-4-methyl-nicotinic acid-N-oxide

HRID 1711151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711151
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5].C(N)(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N+:10]([O-:14])=[C:9]([Cl:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 6761212,6-Dichloro-4-methylpyridine-3-carboxylic acid

Produkt 1

HCID 866295192,6-dichloro-4-methyl-nicotinic acid-N-oxideAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,6-Dichloro-4-methyl-nicotinic acid (0.234 g, 1.14 mmol) and hydrogen peroxide-urea adduct (0.537 g, 5.70 mmol) were suspended in CH2Cl2 to give a white slurry. Trifluoroacetic anhydride (0.65 ml, 4.67 mmol) was added dropwise over 5 minutes and the resulting pale yellow solution was stirred overnight at rt. The reaction mixture was quenched with water (10 ml) and then dry loaded onto silica gel and purified using column chromatography (MeCN/MeOH/NH4OH, 8:1:1, v/v/v) to give 2,6-dichloro-4-methyl-nicotinic acid-N-oxide as a pale yellow crystalline solid (0.103 g, 41%). 1H NMR (CD3OD) δ 2.37 (s, 3H), 7.60 (s, 1H).

Aufarbeitung

  1. customto give a white slurry
  2. customThe reaction mixture was quenched with water (10 ml)
  3. customdry
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-b5406a60f8f04922b3fbc74c06b42ece
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790747B2

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