Phenol → 2-chloro-6-phenyloxypyridine N-oxide

HRID 21696

Reaktionsgleichung

Reaktionsgleichung von HRID 21696
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N+:3]=1[O-:9].[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>CS(C)=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N+:3]=1[O-:9]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 8176732,6-Dichloropyridine N-Oxide

Produkt 1

HCID 540846052-chloro-6-phenyloxypyridine N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The 0.82 g (0.0050 moles) of 2,6-dichloropyridine N-oxide and 0.47 g (0.0050 moles of phenol was reacted with 0.200 g (0.0050 moles) of ground sodium hydroxide in 8.2 ml of DMSO at 80° C. for 6 hours to give 2-chloro-6-phenyloxypyridine N-oxide. It was reacted with 0.600 g (0.015 moles) of ground sodium hydroxide at 80° C. for 3.5 hours to give 1-hydroxy-6-phenyoxypyridine-2-(1H)-one. After cooling, it was added 74 ml of water and was adjusted with 6N HCl to pH 3. The water solution was extracted with dichloromethane (2×25 ml) and was dried over sodium sulfate. The dichloromethane solution was stripped in vacuo to give 1.29 g which was purified with Flash Chromatography (9:1 ethyl acetate:methanol):0.82 (65%).

Quellen und Nachweise

ORD-Eintrag
ord-da3c1dfae2f54a75813ac8e0c23c8be8
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424435

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