Dipropylamine → 2-Chloro-6-methylpyridine-4-carbonitrile

HRID 14231

Reaktionsgleichung

Reaktionsgleichung von HRID 14231
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6].[CH2:11]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH3:13]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6].[CH2:11]([N:14]([CH2:15][CH2:16][CH3:17])[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[N:9]=1)[C:5]#[N:6])[CH2:12][CH3:13]

Komponenten

4

Edukt 2

HCID 8902DipropylamineHCID 210854392-Chloro-6-methylpyridine-4-carbonitrile

Produkt 2

HCID 210854392-Chloro-6-methylpyridine-4-carbonitrileHCID 210854592-(Dipropylamino)-6-methylisonicotinonitrile

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 2-chloro-6-methylisonicotinonitrile (0.230 g, 1.51 mmol) was added di-n-propylamine (5 mL). The mixture was heated at 80° C. in a sealed, thick-walled glass vessel for 12 h and then at room temperature for 17 h. Excess di-n-propylamine was removed under reduced pressure and the residue was partitioned between dichloromethane and aq. sodium bicarbonate. After drying over sodium sulfate and concentration, the residue was chromatographed on silica gel using ethyl acetate-hexane (10/90) to give 0.14 g of 2-chloro-6-methylisonicotinonitrile and 0.059 g of 2-(dipropylamino)-6-methylisonicotinonitrile. Using the above conditions, 2-chloro-6-methylisonicotinonitrile (0.14 g) was converted to an additional 0.043 g of 2-(dipropylamino)-6-methylisonicotinonitrile.

Aufarbeitung

  1. customExcess di-n-propylamine was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and aq. sodium bicarbonate
  3. dry with materialAfter drying over sodium sulfate and concentration
  4. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4846e938218741aeaf262d9689c8572c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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