1,4-Dimethyl 2-oxobutanedioate → HCID 178500753, compound

HRID 922794Notes

Reaction equation

HRID 922794 reaction equation
[NH2:1][C:2]1[C:3]([F:9])=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.O=[C:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:12]([O:14][CH3:15])=[O:13]>CC1C=CC(S(O)(=O)=O)=CC=1>[F:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1/[N:1]=[C:11](\[CH2:16][C:17]([O:19][CH3:20])=[O:18])/[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 2304071,4-Dimethyl 2-oxobutanedioateHCID 227346232-Fluoro-3-methylaniline

Product 1

HCID 178500753HCID 178500753, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

3-Amino-2-fluorotoluene (4.89 g, 39.1 mmol), dimethyl 2-oxobutanedioate (6.26 g, 39.1 mmol), and TosicAcid (0.223 g, 1.172 mmol) were heated at reflux under Dean-Stark conditions for 1 hour. The solvent was removed in vacuo and the residue purified by column chromatography on a silica gel column, eluting with EtOAc/hexane (0-15%) to afford Dimethyl(2E)-2-[(2-fluoro-3-methylphenyl)imino]butanedioate (7-6, 5.48 g, 53% yield) as a clear oil, LCMS shows the compound is 100% pure, LRMS m/z (M+H)+ 268.2 found, 268.1 required.

Workup

  1. temperatureat reflux under Dean-Stark conditions for 1 hour
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by column chromatography on a silica gel column
  4. washeluting with EtOAc/hexane (0-15%)

Sources & evidence

ORD record
ord-494c969230aa4ff5a08a4dce79495522
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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