Dimethylformamide → 5-[(4-Chlorophenyl)methoxy]-2-nitropyridine

HRID 1995838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1995838
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][O:1][C:2]2[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 27628576-Nitropyridin-3-ol

Produkt 1

HCID 204861295-[(4-Chlorophenyl)methoxy]-2-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 5-hydroxy-2-nitropyridine (7 g), K2CO3 (6.9 g) and DMF (100 ml) is stirred for about 10 minutes. To the mixture is added 4-chlorobenzyl chloride (8.1 g) in portions over about 15 minutes. The reaction mixture is stirred about 16 hours and then heated to 45° for about 30 minutes. After cooling, the reaction is diluted with CHCl3, washed with water and saturated NaCl, dried (Na2SO4) and stripped. The crystalline solid is washed with 20% ethyl acetate/hexane, giving 5-(4-chlorobenzyloxy)-2-nitropyridine.

Aufarbeitung

  1. stirringThe reaction mixture is stirred about 16 hours
  2. temperatureheated to 45° for about 30 minutes
  3. temperatureAfter cooling
  4. washwashed with water and saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. washThe crystalline solid is washed with 20% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8574f42884ea46eba38e5ea78c5e082c
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04406689

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