Water → HCID 54193146, compound

HRID 1742816Notes

Reaction equation

HRID 1742816 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[CH:5][CH:4]=1.[CH3:17][N:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:19].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7](=[N:19][N:18]([CH3:17])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 36299N-methyl-N-phenyl-hydrazineHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

Product 1

HCID 54193146HCID 54193146, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 60 ml of acetic acid were dissolved 15 g of ethyl p-methoxybenzoylacetate and 8.25 g of 1-methyl-1-phenylhydrazine and the resulting solution was stirred at room temperature for 12 hours. The reaction mixture was poured into iced water and extracted with ethyl acetate. The extract was washed with aqueous solution of sodium hydrogen carbonate and water in that order, dried over anhydrous magnesium sulfate and concentrated to provide 21.8 g of the desired compound as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with aqueous solution of sodium hydrogen carbonate and water in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e238a32f67344989bfef4abd68cf84c
Source dataset
uspto-grants-1994_08
Patent number
US05342845

Reaction notes

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