Ethanol → m-Bromobenzohydrazide

HRID 2360747Notes

Reaction equation

HRID 2360747 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)C.C(O)C.O.[NH2:17][NH2:18]>O>[Br:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([NH:17][NH2:18])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 90488Ethyl 3-bromobenzoate

Product 1

HCID 520941m-BromobenzohydrazideYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 10 g (44 mmol) of ethyl-3-bromobenzoate was put in a 200-mL three-neck flask, 50 mL of ethanol was added therein, and the mixture was stirred. Thereafter, 12 mL of hydrazine monohydrate was added therein, and the mixture was stirred at 78° C. for 5 hours so as to be reacted. After the reaction, water was added to the reaction solution, and a solid was precipitated. The precipitated solid was collected by suction filtration. The obtained solid was put in approximately 500 mL of water, washed, and again collected by suction filtration; thus, 8.1 g of a white solid that was an object was obtained (yield: 86%).

Workup

  1. stirringthe mixture was stirred at 78° C. for 5 hours so as
  2. customto be reacted
  3. additionwas added to the reaction solution
  4. customa solid was precipitated
  5. filtrationThe precipitated solid was collected by suction filtration
  6. washwashed
  7. filtrationagain collected by suction filtration
  8. customwas obtained (yield: 86%)

Sources & evidence

ORD record
ord-95eafb51ef4c4ef7bb06861a2ada62d8
Source dataset
uspto-grants-2014_04
Patent number
US08686159B2

Reaction notes

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