Acetic Acid → HCID 70181045, compound

HRID 564904Notes

Reaction equation

HRID 564904 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=O)[CH2:11][CH3:12].C(O)(=O)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([CH2:11][CH3:12])=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70002-MethoxyanilineHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 70181045HCID 70181045, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of o-anisidine (15.11 g), ethyl propionylacetate (17.69 g) and acetic acid (0.5 ml) in benzene (30 ml) was refluxed removing water for 24 hours. The solvent was removed in vacuo, and the residue was dissolved in toluene (30 ml). The reaction mixture was refluxed for an additional 8 hours. The solvent was removed in vacuo. The residue was purified by column chromatography (hexane-ethyl acetate) to give ethyl 3-(2-methoxyanilino)-2-pentenoate (15.11 g) as an oil.

Workup

  1. temperaturewas refluxed
  2. customremoving water for 24 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in toluene (30 ml)
  5. temperatureThe reaction mixture was refluxed for an additional 8 hours
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c89f36a681d04b2285effcbcc494a365
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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