Aniline → 2-Butenedioic acid, 2-(phenylamino)-, diethyl ester, (E)-

HRID 1650108Notes

Reaction equation

HRID 1650108 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:9][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=O>C1(C)C=CC=CC=1>[C:2]1([NH:1][C:9]([C:8]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 66951Diethyl oxalacetate

Product 1

HCID 5888822-Butenedioic acid, 2-(phenylamino)-, diethyl ester, (E)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aniline (0.217 mol) and diethyl oxalacetate (0.217 mol) are mixed in toluene (500 ml) and heated to reflux, i.e., about 100° C., under a water separator for approximately one hour. The toluene is then removed under vacuum to afford the desired product, i.e., diethyl 3-phenylaminobut-2-ene-dioate.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customThe toluene is then removed under vacuum

Sources & evidence

ORD record
ord-6f1e8b0184fb4b9b810d0de5e6e7876b
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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