Aniline → HCID 12213510, compound

HRID 1195649Notes

Reaction equation

HRID 1195649 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([C:14]([O:16][CH3:17])=[O:15])#[C:9][C:10]([O:12][CH3:13])=[O:11]>CO>[NH:1](/[C:9](=[CH:8]\[C:14]([O:16][CH3:17])=[O:15])/[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 12213510HCID 12213510, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Purified aniline (15.0 g, 0.16 mole) was reacted with dimethyl acetylenedicarboxylate (19.8 ml, 0.15 mole) in 400 ml methanol according to the procedure of Heindel, et al., J. Het. Chem. 1966, 3, 222. The reaction was refluxed for 18 hours, then worked up by evaporating the solvent, dissolving the residue in ether, and washing consecutively with 0.5 N HCl, H2O, and sat. NaCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel in 80/20 hexane/EtOAc which yielded 29.14 g of the Michael Adduct, dimethyl anilinofumarate as a light yellow oil.

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. customby evaporating the solvent
  3. dissolutiondissolving the residue in ether
  4. washwashing consecutively with 0.5 N HCl, H2O, and sat. NaCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel in 80/20 hexane/EtOAc which

Sources & evidence

ORD record
ord-bf799f4cd8e641d090b526a500251b7d
Source dataset
uspto-grants-1992_05
Patent number
US05112821

Reaction notes

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