2-Fluoroaniline → HCID 13922969, compound

HRID 922791Notes

Reaction equation

HRID 922791 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([C:15]([O:17][CH3:18])=[O:16])#[C:10][C:11]([O:13][CH3:14])=[O:12]>CO>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4]/[C:10](=[CH:9]/[C:15]([O:17][CH3:18])=[O:16])/[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 13922969HCID 13922969, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution 2-fluoroaniline (1.00 g, 9.00 mmol) in MeOH (11.1 mL) at 0° C. was added dimethyl acetylenedicarboxylate (DMAD, 1.34 mL, 10.8 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 0-25% EtOAc in Hexanes) to give dimethyl(2E)-2-[(2-fluorophenyl)amino]but-2-enedioate (7-1, 1.9 g, 83%). LRMS m/z (M+H)+ 254.4 found, 254.4 required.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel flash chromatography (gradient 0-25% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-be97227f34bb458c94ceefd604cf3563
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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