1,2-Dichloroethane → 2-Chloro-3-methyl-5-nitropyridine

HRID 508467

Reaktionsgleichung

Reaktionsgleichung von HRID 508467
[CH3:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[Cl:12]CCCl.[Cl-].[P+]=O>CN(C=O)C>[Cl:12][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 178428770HCID 178428770, VerbindungHCID 178527006HCID 178527006, Verbindung

Produkt 1

HCID 896482-Chloro-3-methyl-5-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 350 ml three-necked round-bottomed flask equipped with a magnetic bar, a thermometer, a dropping funnel and a reflux condenser is charged with 3-methyl-5-nitro-pyridin-2-ol (23.1 g), and 1,2-dichloroethane (150 ml). Phosphorous oxide chloride (17 ml) is added dropwise. Into this mixture DMF (11.5 ml) is added dropwise at room temperature. The reaction mixture is heated at 70° C. under stirring for 0.5 hour. After cooling the mixture to ambient temperature, it is concentrated in vacuo at 50° C., to obtain a brown oily gum. Purification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v) gives 23.34 g of the compound as a light yellow solid (MP: 40-42° C.).

Aufarbeitung

  1. customA 350 ml three-necked round-bottomed flask equipped with a magnetic bar
  2. temperatureAfter cooling the mixture to ambient temperature
  3. concentrationit is concentrated in vacuo at 50° C.
  4. customto obtain a brown oily gum
  5. customPurification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v)

Quellen und Nachweise

ORD-Eintrag
ord-082a935ede014b0ab270a3492d879cd2
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096525B2

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