4-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide Hydrochloride → [1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate

HRID 1659164Notes

Reaction equation

HRID 1659164 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)N)=[CH:6][CH:5]=1.C(O[CH2:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])(=O)CCC(C)=O>C(O)(=O)C>[C:30]([O:32][CH:33]([O:32][C:30](=[O:31])[CH2:29][C:33]1[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:9]=2)[N:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:34]=1[CH3:35])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:31])[CH3:29]

Participants

4

Reactant 2

HCID 124352824-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide HydrochlorideHCID 126583762-Oxo-2-(phenylmethoxy)ethyl 4-oxopentanoate

Product 1

HCID 70621351[1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5 g (0.016 mol) of N(1) -(p-methoxyphenyl)-p-chlorobenzhydrazide hydrochloride and 4.75 g (0.018 mol) of benzyl levulinoyloxyacetate were heated in 25ml of glacial acetic acid for 3 hours at 80°C. The solvent was then evaporated off under vacuum, the residue was taken up in chloroform and the solution was washed neutral by shaking with sodium bicarbonate solution and thereafter with water. After drying the chloroform solution, this was subjected to chromatography on aluminium oxide, the eluate was concentrated by evaporation and the viscous oil remaining as residue was crystallised by adding ether. The compound melted at 94°-95°C. The yield was 4.1 g which corresponds to 50.7% of the theoretical yield.

Workup

  1. customThe solvent was then evaporated off under vacuum
  2. washthe solution was washed neutral
  3. dry with materialAfter drying the chloroform solution
  4. concentrationthe eluate was concentrated by evaporation
  5. customwas crystallised
  6. additionby adding ether

Sources & evidence

ORD record
ord-5f9d84a0ff96432c918522a909fff0bb
Source dataset
uspto-grants-1976_06
Patent number
US03966956

Reaction notes

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