P-Anisidine → HCID 178469291, compound

HRID 1865437Notes

Reaction equation

HRID 1865437 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13]([C:15]#[C:16][C:17](OCC)=[O:18])=[O:14])[CH3:11]>CO>[OH:18][C:17]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[N:9]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH:16]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 178469291HCID 178469291, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of p-anisidine (2.7 g, 22 mmol) in methanol (50 mL) was added diethyl-acetylene dicarboxylate (3.74 g, 22 mmol). The resulting solution was heated at 55° C. for 1 hour. The reaction mixture was concentrated in vacuo. The residue was dissolved in phenyl ether (40 mL) and refluxed at 240° C. for 1 hour. The reaction mixture was cooled to room temperature, diluted with hexanes and filtered. A light brown solid was obtained. LC-MS: 1.39 min; (M+H)=248.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in phenyl ether (40 mL)
  3. temperaturerefluxed at 240° C. for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additiondiluted with hexanes
  6. filtrationfiltered
  7. customA light brown solid was obtained
  8. custom1.39 min

Sources & evidence

ORD record
ord-cf8e4485cc0a4ebd84d20895d637d73a
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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