Reaction #1265374

Reaction equation

ethyl 2-chloronicotinate

4-(N,N-dimethylaminomethyl)styrene

triethylamine

tri(o-tolyl)phosphine

→

product

Yield 33.9%

Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)nicotinate

Yield 33.9%

Solvents

water

dimethylformamide

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was then concentrated in vacuo
2. 2
   Otherthe resulting residue was partitioned between ethyl acetate and water
3. 3
   OtherThe organic phase was separated off
4. 4
   Washwashed with water
5. 5
   Otherdried
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe residue was then crystallized as oxalate from isopropanol
8. 8
   workup.ADDITIONafter addition of an equivalent amount of oxalic acid

Procedure

6.7 g (39 mmol) of ethyl 2-chloronicotinate, 8.2 g (51 mmol) of 4-(N,N-dimethylaminomethyl)styrene, 9.9 g (98 mmol) of triethylamine, 0.36 g of palladium(II) acetate and 0.96 [lacuna] of tri(o-tolyl)phosphine were mixed in 150 ml of dimethylformamide and, after addition of 1 ml of water, stirred at 140° C. for 13 h. The reaction mixture was then concentrated in vacuo, and the resulting residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with water, dried and concentrated in vacuo. The residue was then crystallized as oxalate from isopropanol after addition of an equivalent amount of oxalic acid. 4.1 g (27%) of the product were obtained as monooxalate.

Source