Dimethyl acetylenedicarboxylate → Dimethyl 2-(2-cyanoanilino)fumarate

HRID 1449566Notes

Reaction equation

HRID 1449566 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([C:16]([O:18][CH3:19])=[O:17])#[C:11][C:12]([O:14][CH3:15])=[O:13]>C(O)(C)(C)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1]/[C:11](=[CH:10]\[C:16]([O:18][CH3:19])=[O:17])/[C:12]([O:14][CH3:15])=[O:13])#[N:5]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 729132-Aminobenzonitrile

Product 1

HCID 12842189Dimethyl 2-(2-cyanoanilino)fumarateYield 44.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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).

Workup

  1. customa precipitate formed
  2. filtrationwas collected by filtration
  3. washThe material was washed with cold methanol and air
  4. customdried

Sources & evidence

ORD record
ord-b5a43c0bc09a42f5a3f06d2f6ffcfc09
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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