Ethanol → 4-Bromobenzohydrazide

HRID 1399468Notes

Reaction equation

HRID 1399468 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)C.C(O)C.O.[NH2:17][NH2:18]>O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([NH:17][NH2:18])=[O:3])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 22043Ethyl 4-bromobenzoateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 222194-BromobenzohydrazideYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
78 °C

Procedure

Into a 200 mL three-neck flask was put 25 g (0.19 mol) of ethyl-4-bromobenzoate, 50 mL of ethanol was added thereto, and the mixture was stirred. After that, 20 mL of hydrazine monohydrate was added to the mixture, and then the mixture was stirred while being heated at 78° C. for 5 hours to be reacted. After the reaction, water was added to the reaction mixture, and a precipitated solid was collected by suction filtration. The obtained solid was washed with water and collected by suction filtration, whereby 24 g of a white solid of 4-bromobenzoylhydrazine, which was the object of the synthesis, was obtained in a yield of 96% (synthesis scheme (a-1)).

Workup

  1. customInto a 200 mL three-neck flask was put
  2. stirringthe mixture was stirred
  3. customto be reacted
  4. additionwas added to the reaction mixture
  5. filtrationa precipitated solid was collected by suction filtration
  6. washThe obtained solid was washed with water
  7. filtrationcollected by suction filtration, whereby 24 g of a white solid of 4-bromobenzoylhydrazine, which
  8. customthe object of the synthesis
  9. customwas obtained in a yield of 96% (synthesis scheme (a-1))

Sources & evidence

ORD record
ord-2cbc675418a74ce9a9c5370f60d15472
Source dataset
uspto-grants-2014_12
Patent number
US08906518B2

Reaction notes

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