Acetic Acid → ethyl 3-(4-chloroanilino)but-2-enoate

HRID 2187665Notes

Reaction equation

HRID 2187665 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=O.C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]([CH3:13])=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 78124-ChloroanilineHCID 8868Ethyl Acetoacetate

Product 1

HCID 38739ethyl 3-(4-chloroanilino)but-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 70 g (0.54 mol) of 4-chloroaniline, 70 ml (0.54 mol) of ethyl acetoacetate, and 0.6 ml acetic acid in 400 ml toluene was heated in a Dean-Stark apparatus for 19 at 130° C. The mixture was evaporated, and the remaining crystalline precipitate stirred with diisopropylether and filtered. The filtrate was concentrated and the residue purified via column chromatography on silica gel with dichloromethane/hexane 4:1.

Workup

  1. customThe mixture was evaporated
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified via column chromatography on silica gel with dichloromethane/hexane 4:1

Sources & evidence

ORD record
ord-25f4e5947d4f4c47a184d35ec991489a
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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