Tetrahydrofuran → 6-Chloro-3-nitropyridine-2-carbonitrile

HRID 475325

Reaktionsgleichung

Reaktionsgleichung von HRID 475325
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C1COCC1.[C-]#[Si+].[C:19]([Cu])#[N:20]>O.CN1C(=O)CCC1>[Cl:11][C:4]1[N:3]=[C:2]([C:19]#[N:20])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 9863Silicon carbideHCID 852392,6-Dichloro-3-nitropyridineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

2,6-dichloro-3-nitro-pyridine (2.5 g, 12.9 mmol) is taken up in a solvent mixture of THF and NMP (5:1, 13 mL), combined with two spatula tips of silicon carbide and CuCN (2.3 g, 26.0 mmol) and heated to 180° C. in the microwave reactor for 45 min. Then the solid obtained is suspended in H2O, extracted with ethyl acetate, washed with NaCl-sln., the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and 6-chloro-3-nitro-pyridine-2-carbonitrile (HPLC-MS: tRet.=1.01 min, MS(M+H)+=182, method LCMSBAS1) is obtained.

Aufarbeitung

  1. customThen the solid obtained
  2. extractionextracted with ethyl acetate
  3. washwashed with NaCl-sln
  4. custom, the organic phase is dried on MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-2fdef5b7fcb34352928a4433b75f0f57
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637549B2

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