Reaktion #466593

Reaktionsgleichung

KMnO4

6-chloro-N-methyl-nicotinamide

o-tolylmagnesium chloride

NH4Cl

→

product

Ausbeute 78.9%

6-Chloro-N-methyl-4-o-tolyl-nicotinamide

Ausbeute 78.9%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 4° C.
2. 2
   SonstigeThe aqueous phase was separated
3. 3
   Extraktionextracted twice with THF
4. 4
   Waschenthe organic phases were washed twice with 5% aqueous NH4Cl
5. 5
   TrocknenThe combined organic phases were dried over Na2SO4
6. 6
   workup.STIRRINGThe reaction mixture was stirred for 5.5 h at r.t.
7. 7
   Filtrationfiltrated
8. 8
   Sonstigethe solvent was removed
9. 9
   SonstigeThe residue was purified by chromatography over silica gel (CHCI3)

Vorschrift

A solution of 1.5 g (8.8 mmol) 6-chloro-N-methyl-nicotinamide in 18 ml THF was added at 4° C. over 15 min to a solution of 21.9 ml (21.9 mmol) o-tolylmagnesium chloride 1M in THF. The reaction mixture was stirred at r.t. for 2 h cooled to 4° C. and treated dropwise over 10 min with 30.0 ml 5% aqueous NH4Cl. The aqueous phase was separated and extracted twice with THF and the organic phases were washed twice with 5% aqueous NH4Cl. The combined organic phases were dried over Na2SO4 and subsequently treated at r.t. in four portions over 10 h with 0.9 g (5.7 mmol) KMnO4. The reaction mixture was stirred for 5.5 h at r.t., filtrated and the solvent was removed. The residue was purified by chromatography over silica gel (CHCI3) to yield 1.8 g (78.9%) product as a yellow oil.

Quelle