m-Toluidine → HCID 178469287, compound

HRID 1185419Notes

Reaction equation

HRID 1185419 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH2:9]([O:11][C:12](=[O:20])[C:13]#[C:14][C:15](OCC)=[O:16])[CH3:10]>CO>[CH2:9]([O:11][C:12]([C:13]1[CH:14]=[C:15]([OH:16])[C:4]2[C:3](=[CH:2][C:1]([CH3:8])=[CH:6][CH:5]=2)[N:7]=1)=[O:20])[CH3:10]

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 178469287HCID 178469287, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15.5 g of m-Tolylamine in 130 ml of methanol, 24.6 g of but-2-ynedioic acid diethyl ester was added drop-wise over 30 min at 0° C. and stirred for 3 h at RT. Then, the solvents were removed under reduced pressure and the residue was dissolved in 70 ml of Dowtherm® and heated to 250° C. for 2 h. Then, the reaction mixture was allowed to cool to RT and 300 ml of n-heptane was added to precipitate the crude product, which was collected by filtration. The title compound was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 9.7 g.

Workup

  1. customThen, the solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 70 ml of Dowtherm®
  3. temperatureheated to 250° C. for 2 h
  4. temperatureto cool to RT
  5. addition300 ml of n-heptane was added
  6. customto precipitate the crude product, which
  7. filtrationwas collected by filtration
  8. customThe title compound was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  9. additionThe fractions containing the product
  10. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-44a62cc07fcd4f89a8595ec7a535532d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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