Aniline → Ethyl 3-anilinobut-2-enoate

HRID 1165597

Reaction equation

HRID 1165597 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:16])[CH2:12][C:13]([CH3:15])=O)[CH3:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:8]([O:10][C:11](=[O:16])[CH:12]=[C:13]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:15])[CH3:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8868Ethyl AcetoacetateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 94928Ethyl 3-anilinobut-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Aniline (0.20 mol) and ethylacetoacetate (0.20 mol) are mixed in toluene (200 mL) containing 0.04 g of p-toluenesulfonic acid-hydrate and heated at reflux under a water separator for one hour. The toluene is removed under vacuum to afford the ethyl-3-phenylaminobut-2-enoate which can be used as is for the preparation of the ethyl 2-methyl-3-quinolinecarboxylate.

Workup

  1. temperatureheated
  2. temperatureat reflux under a water
  3. customThe toluene is removed under vacuum

Sources & evidence

ORD record
ord-94f9fe33b8f246e79fa026b72244ccc5
Source dataset
uspto-grants-1990_03
Patent number
US04910327

Linked notes

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