Sodium Hydroxide → 5-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine

HRID 2380255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2380255
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([N:11]([CH3:13])[CH3:12])[N:3]=1.[Br:14]Br.[OH-].[Na+]>C(O)(=O)C.O>[Br:14][C:5]1[C:6]([CH3:10])=[C:7]([C:8]#[N:9])[C:2]([Cl:1])=[N:3][C:4]=1[N:11]([CH3:12])[CH3:13]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 199600452-Chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine

Produkt 1

HCID 199600285-bromo-2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridineAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 2-chloro-3-cyano-6-(N,N-dimethylamino)-4-methylpyridine (0.98 g) in acetic acid (10 mL) was added bromine (0.9 g) in acetic acid (1 mL). The reaction mixture was stirred at room temperature for 20 minutes and then warmed to 60° C. for 5 minutes. After cooling to room temperature the mixture was poured into a solution of sodium hydroxide (8 g) in water (100 mL). The mixture was extracted with chloroform (3×30 mL). The combined organic phase was washed, dried, and evaporated to give 1.36 g of the title compound, suitable for use in the next reaction.

Aufarbeitung

  1. temperaturewarmed to 60° C. for 5 minutes
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionThe mixture was extracted with chloroform (3×30 mL)
  4. washThe combined organic phase was washed
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b2a1d09edd3840d3ba41cb9b3bf14114
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05366972

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