Thionyl Chloride → 2-Chloro-4-methyl-5-nitropyridine

HRID 1681281

Reaktionsgleichung

Reaktionsgleichung von HRID 1681281
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][NH:5][C:4](=O)[CH:3]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 3453714-Methyl-5-nitro-1,2-dihydropyridin-2-one

Produkt 1

HCID 3453642-Chloro-4-methyl-5-nitropyridineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated at reflux under nitrogen for 52 hours. The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride. The residual oil then passed through a silica gel filter (dried at 150° C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1). This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95%) as an orange oil, which crystallized below 0° C.; IR (CHCl3) 1,605, 1,550, 1,520, 1,450, 1,360, 1,345 cm-1 ; 1H NMR (CDCl3) δ 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100 (55), 99 (74), 90 (43), 75 (36).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 52 hours
  3. customThe resultant orange colored solution was evaporated under reduced pressure
  4. additiona small amount of anhydrous toluene was added
  5. customremoved via evaporation under reduced pressure
  6. customto remove traces of thionyl chloride
  7. filtrationfilter
  8. custom(dried at 150° C. under vacuum overnight, approximately 100 g)
  9. customThis filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5b8cef8327204f4b90a1b71cbd1bd78d
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169947

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