Acetic Acid → Ethyl 3-(2-methoxyanilino)-2-methyl-2-butenoate

HRID 1604571Notes

Reaction equation

HRID 1604571 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(O)(=O)C.[C:14]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[CH3:15]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:14]([CH3:15])=[C:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 701Ethyl 2-methylacetoacetateHCID 70002-Methoxyaniline

Product 1

HCID 67566028Ethyl 3-(2-methoxyanilino)-2-methyl-2-butenoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-methoxyaniline (10 g), acetic acid (1 ml) and ethyl 2-acetylpropionate (12.3 g) in benzene (30 ml) was refluxed for 24 hours, and then the solvent was removed to give crude ethyl 3-(2-methoxyanilino)-2-methyl-2-butenoate, which was used as a starting compound at the following example without further purification.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-074ae69a55d343abad7b707f2f790133
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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