Réaction #3214

Équation de réaction

2-aminobenzonitrile

dimethyl acetylenedicarboxylate

→

solid

Rendement 44.3%

Dimethyl 2-(2-cyanoanilino)fumarate

Rendement 44.3%

Solvants

t-butanol

Conditions de réaction

Traitement

1. 1
   Autrea precipitate formed
2. 2
   Filtrationwas collected by filtration
3. 3
   LavageThe material was washed with cold methanol and air
4. 4
   Autredried

Mode opératoire

A solution of 2-aminobenzonitrile (5.00 g, 42.3 mM) and dimethyl acetylenedicarboxylate (6.42 g, 45.2 mM) in t-butanol (70.5 mL) was refluxed under a nitrogen atmosphere for 12 hr. After cooling the reaction mixture to room temperature, a precipitate formed and was collected by filtration. The material was washed with cold methanol and air dried to give a yellow solid (4.88 g). Recrystallization of this solid from methanol provided the title compound (4.39 g, 39.9%) as yellow crystals, mp 116.5°-117.5° C.; MS(CI): 261 (M+H). Analysis for C13H12N2O4 : Calculated: C, 60.00; H, 4.65; N, 10.76 Found: C, 60.03; H, 4.67; N, 10.84

Source