Benzene → Ethyl 3-(3,4-dimethoxyanilino)but-2-enoate

HRID 328804Notes

Reaction equation

HRID 328804 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O.C1C=CC=CC=1>C(O)(=O)C>[CH2:19]([O:18][C:12](=[O:17])[CH:13]=[C:14]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=1)[CH3:16])[CH3:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 8868Ethyl AcetoacetateHCID 227703,4-Dimethoxyaniline

Product 1

HCID 70638975Ethyl 3-(3,4-dimethoxyanilino)but-2-enoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Aminoveratrole (62.0 g.), ethyl acetoacetate (63.0 g.), benzene (375 ml.), and acetic acid (2.1 ml.) are combined and refluxed in a flask equipped with a Dean-Stark strap to remove water until thin layer chromatography indicated the reaction is complete. The solvent is removed under reduced pressure to give a dark oil which crystallized upon standing. Recrystallization from hexane gives 79.0 g. of a tan powder, m.p. 59°-60° ; a second drop afforded 6.7 g., m.p. 54°-56° . A sample is recrystallized from ethanol/water to give an analytical sample, m.p. 57°-58°.

Workup

  1. temperaturerefluxed in a flask
  2. customequipped with a Dean-Stark strap
  3. customto remove water until thin layer chromatography
  4. customThe solvent is removed under reduced pressure
  5. customto give a dark oil which
  6. customcrystallized
  7. customRecrystallization from hexane
  8. customgives 79.0 g
  9. customa second drop afforded 6.7 g
  10. customA sample is recrystallized from ethanol/water
  11. customto give an analytical sample, m.p. 57°-58°

Sources & evidence

ORD record
ord-fde46578f0da425cbc8e110d0d42ede2
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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