Acetic Acid → HCID 86590933, compound

HRID 889827Notes

Reaction equation

HRID 889827 reaction equation
[CH3:1][N:2]([CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=O)[C:3]([O:5][CH3:6])=[O:4].C(O)(=O)C.O.[NH2:22][NH2:23]>C(O)CC>[CH3:1][N:2]([CH2:7][C:8](=[N:22][NH2:23])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 22248800HCID 22248800, compound

Product 1

HCID 86590933HCID 86590933, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

101 g (418 mmol) of 2-(N-methyl-N-(methoxycarbonyl)-amino)-4′-chloroacetophenone was dissolved in 600 ml of warm 1-propanol. To this mixture was added 4.85 g (80 mmol) of acetic acid and 60.9 g (1218 mmol) of hydrazine monohydrate. The mixture was refluxed for two hours and then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water and saturated aqueous sodium chloride. After drying over magnesium sulfate, filtering, and reconcentrating in vacuo, there was obtained 75.6 g of the title compound, an oil.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationfiltering

Sources & evidence

ORD record
ord-4f95c70f74784c8587d1267e7c10534e
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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