Dimethyl acetylenedicarboxylate → HCID 178500753, compound

HRID 922802Notes

Reaction equation

HRID 922802 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[F:11][C:12]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14]>CO>[F:11][C:12]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:13]=1/[N:14]=[C:2](\[CH2:1][C:7]([O:9][CH3:10])=[O:8])/[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 227346232-Fluoro-3-methylaniline

Product 1

HCID 178500753HCID 178500753, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., dimethyl acetylenedicarboxylate (8.70 mL, 70.4 mmol) was added dropwise to a solution 2-fluoro-3-methylaniline (7.34 g, 58.7 mmol) in MeOH (58.7 mL). After stirring at room temperature overnight, the reaction mixture was concentrated to dryness. The residue was purified by silica gel flash chromatography (gradient 0-60% EtOAc/Hexanes) to give (E)-dimethyl 2-(2-fluoro-3-methylphenylimino)succinate (7-14, 14.59 g, 93%). LRMS m/z (M+H)+ 268.3 found, 268.1 required.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customThe residue was purified by silica gel flash chromatography (gradient 0-60% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-0328aaa2d3644bdeacbbc1476b899f3a
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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