Reaktion #466614

Reaktionsgleichung

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

o-Tolylmagnesium chloride

6-chloro-N,N-diethyl-nicotinamide

methanol

→

6-chloro-N,N-diethyl-4-o-tolyl-nicotinamide

Ausbeute 87.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled again to 0° C.
2. 2
   workup.STIRRINGAfter stirring 2 hours at room temperature
3. 3
   Einengenthe reaction mixture was concentrated under reduced pressure and 50 ml t-butyl-methylether
4. 4
   workup.ADDITIONwere added at 50° C
5. 5
   FiltrationThe resulting suspension was filtered off
6. 6
   Einengenthe filtrate was concentrated
7. 7
   Sonstigethe residue was purified by flash chromatography (eluent: ethyl acetate/n-heptane 1:1)

Vorschrift

7.62 ml (7.62 mMol) o-Tolylmagnesium chloride solution (1M in THF) were added over 15 minutes to a solution of 0.60 g (2.54 mMol) 6-chloro-N,N-diethyl-nicotinamide in 3.0 ml THF cooled to 0° C. The reaction mixture was stirred 2 hours at room temperature, then cooled again to 0° C. and 0.41 ml methanol (10.1 mMol) were added followed by 692 mg 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.1 mMol). After stirring 2 hours at room temperature, the reaction mixture was concentrated under reduced pressure and 50 ml t-butyl-methylether were added at 50° C. The resulting suspension was filtered off, the filtrate was concentrated and the residue was purified by flash chromatography (eluent: ethyl acetate/n-heptane 1:1) to yield 0.67 g (86%) of 6-chloro-N,N-diethyl-4-o-tolyl-nicotinamide as a yellow oil.

Quelle