Hydrazine hydrate (1:1) → 2-Hydrazinylidene-1,2-bis(3-methoxyphenyl)ethan-1-one

HRID 436385Notes

Reaction equation

HRID 436385 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[O:15])=O)[CH:9]=[CH:10][CH:11]=1>C(O)C.C(O)(=O)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[N:2][NH2:3])[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[O:15])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1234931,2-Ethanedione, 1,2-bis(3-methoxyphenyl)-

Product 1

HCID 713859832-Hydrazinylidene-1,2-bis(3-methoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of 1.0 g hydrazine hydrate in 25 ml ethanol is added a warm solution of 3,3'-dimethoxybenzil, 7.0 g in 125 ml ethanol. The solution is heated to 65° C for 48 hours. Three drops of acetic acid are added and heating is continued for 48 hours. The solution is concentrated, diluted with 100 ml water and extracted with methylene chloride. The organic layer is removed, dried over magnesium sulfate and the solvent removed. The oily residue is chromatographed on 200 g of BioSil-A using chloroform-benzene mixtures. Elution of product is completed with methylene chloride. The product from chromatography is recrystallized from chloroform-hexane yielding 2.8 g of pale yellow needles. M.P. 109°-110.5°.

Workup

  1. temperatureheating
  2. concentrationThe solution is concentrated
  3. additiondiluted with 100 ml water
  4. extractionextracted with methylene chloride
  5. customThe organic layer is removed
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed
  8. customThe oily residue is chromatographed on 200 g of BioSil-A
  9. washElution of product
  10. customThe product from chromatography is recrystallized from chloroform-hexane yielding 2.8 g of pale yellow needles

Sources & evidence

ORD record
ord-fc7232a290a84d0e8387431e2ac57da6
Source dataset
uspto-grants-1977_02
Patent number
US04009022

Reaction notes

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