Dimethyl acetylenedicarboxylate → HCID 69930317, compound

HRID 1497339Notes

Reaction equation

HRID 1497339 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[C:10]([C:16]([O:18][CH3:19])=[O:17])#[C:11][C:12]([O:14][CH3:15])=[O:13]>CO>[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4]/[C:11](=[CH:10]/[C:16]([O:18][CH3:19])=[O:17])/[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 677752,5-Difluoroaniline

Product 1

HCID 69930317HCID 69930317, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution 2,5-difluoroaniline (X1) (3.00 mL, 29.9 mmol) in MeOH (30 mL) was added dimethyl acetylenedicarboxylate (P2) (DMAD, 4.44 mL, 35.9 mmol). The reaction was stirred at room temperature for 2 h. The mixture was concentrated and the residue was purified by silica gel flash chromatography (gradient 0-30% EtOAc in Hex) to give dimethyl (2E)-2-[(2,5-difluorophenyl)amino]but-2-enedioate (X2). ES-MS [M+1]+=272.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel flash chromatography (gradient 0-30% EtOAc in Hex)

Sources & evidence

ORD record
ord-1bdee552afc048c483e85eb2a26d4902
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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