Methanol → 2-(4-Fluorophenylamino)but-2-enedioic Acid Dimethyl Ester

HRID 2377794Notes

Reaction equation

HRID 2377794 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([C:14]([O:16][CH3:17])=[O:15])#[C:10][C:11]([O-:13])=[O:12].[CH3:18]O>>[CH3:17][O:16][C:14](=[O:15])[C:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:10][C:11]([O:13][CH3:18])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 97314-FluoroanilineHCID 86613298Methyl acetylene-dicarboxylate

Product 1

HCID 691174942-(4-Fluorophenylamino)but-2-enedioic Acid Dimethyl Ester

Conditions

Temperature
55 °C

Procedure

50 ml (0.51 M) of 4-fluoroaniline (at 98%) are introduced into 500 ml of anhydrous methanol, followed by dropwise addition of 70.5 ml (0.56 M) of methyl acetylenedicarboxylate (at 98%). The reaction mixture is heated at 55° C. with stirring for 3 hours, and then evaporated under reduced pressure. The residue is purified by evolution through silica.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue is purified by evolution through silica

Sources & evidence

ORD record
ord-7569ed16d16740f0b1a7f10ce6bff34a
Source dataset
uspto-grants-2008_12
Patent number
US07470708B2

Reaction notes

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