4-Chloro-3-methylaniline → HCID 178469290, compound

HRID 1185555Notes

Reaction equation

HRID 1185555 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13](=[O:21])[C:14]#[C:15][C:16](OCC)=[O:17])[CH3:11]>CO>[CH2:10]([O:12][C:13]([C:14]1[CH:15]=[C:16]([OH:17])[C:7]2[C:5](=[CH:4][C:3]([CH3:9])=[C:2]([Cl:1])[CH:8]=2)[N:6]=1)=[O:21])[CH3:11]

Participants

4

Reactant 2

HCID 235364-Chloro-3-methylanilineHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 178469290HCID 178469290, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.5 g of 4-chloro-3-methylaniline in 30 ml of methanol, 4.2 g of but-2-ynedioic acid diethyl ester were added dropwise 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 were 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: 1.1 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 were 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-f1ff7f43688245f1ba836ff9f8962e84
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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