Water → Benzyl levulinoyloxyacetate (p-methoxyphenyl)-hydrazone

HRID 1659166Notes

Reaction equation

HRID 1659166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.O.[C:12]([O:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O)(=[O:18])[CH2:13][CH2:14][C:15]([CH3:17])=[O:16]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:20][O:19][C:12](=[O:18])[CH2:13][CH2:14][C:15]([CH3:17])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77023(4-Methoxyphenyl)hydrazineHCID 126583762-Oxo-2-(phenylmethoxy)ethyl 4-oxopentanoate

Product 1

HCID 86733639Benzyl levulinoyloxyacetate (p-methoxyphenyl)-hydrazoneYield 104.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.2 g of p-methoxyphenylhydrazine were suspended in 25 ml of glacial acetic acid and 90 ml of water and 10 g of benzyl levulinoyloxyacetate were slowly added at room temperature while stirring. After stirring for 1 hour, the mixture was extracted by shaking with toluene, the toluene solution was washed neutral with water, dried and concentrated. 15.1 g of benzyl levulinoyloxyacetate (p-methoxyphenyl)-hydrazone were obtained as a brownish oil, which was not purified but was dissolved in 25 ml of absolute pyridine, and then 100 ml of ether were added and mixed with a solution of 8.7 g of p-chlorobenzoyl chloride in 50 ml of ether at 0°C with the introduction of nitrogen. After boiling for 2 hours under nitrogen, the solution was cooled, washed neutral with water, dried and concentrated by evaporation. 19 g (crude yield) of N(2) -(p-chlorobenzoyl)-N(2) -(p-methoxyphenyl)-hydrazone of benzyl levulinoyloxyacetate were obtained. This product was further treated without purification, by taking it up in 75 ml of glacial acetic acid and heating for 5 hours at 80°C. After evaporating off the glacial acetic acid under vacuum, the further treatment was carried out as described in Example 1. The yield of [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate amounted to 11% of the theoretical, based on the total amount of hydrazine.

Workup

  1. stirringAfter stirring for 1 hour
  2. extractionthe mixture was extracted
  3. stirringby shaking with toluene
  4. washthe toluene solution was washed neutral with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-77221c1f579e4111a7ce79d6ab42ccd5
Source dataset
uspto-grants-1976_06
Patent number
US03966956

Reaction notes

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