Acetic Acid → HCID 67832148, compound

HRID 1029439Notes

Reaction equation

HRID 1029439 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][O:11][CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(O)(=O)C.S([O-])([O-])(=O)=O.[Ca+2]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:13]([CH2:12][O:11][CH3:10])=[CH:14][C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70002-MethoxyanilineHCID 24497Calcium SulfateHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 67832148HCID 67832148, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 100 g of o-anisidine, 190 g of methyl γ-methoxyacetoacetate, 2.3 ml of acetic acid, 203 g of calcium sulfate and 800 ml of absolute ethanol was refluxed for 16 hours. The residue after filtration and concentration of the filtrate under reduced pressure was taken up in ethyl acetate, the solution was extracted several times with 2 N NaOH and 5% strength citric acid solution and dried over Na2SO4, and the solvent was removed in a rotary evaporator. 150 g of crude product were obtained and were employed without further purification in the following stage.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe residue after filtration and concentration of the filtrate under reduced pressure
  3. extractionthe solution was extracted several times with 2 N NaOH and 5% strength citric acid solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-1c2e12bc748a4c769c1e6c3b27a0bf9e
Source dataset
uspto-grants-1992_04
Patent number
US05102892

Reaction notes

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