Methyl 3-bromobenzoate → m-Bromobenzohydrazide

HRID 1052603Notes

Reaction equation

HRID 1052603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].O.[NH2:13][NH2:14]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:13][NH2:14])=[O:6]

Participants

4

Reactant 2

HCID 12070Methyl 3-bromobenzoateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 520941m-BromobenzohydrazideYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-bromobenzoate (2 g, 9.3 mmol) was dissolved in 25 ml ethanol. Hydrazine hydrate (4.5 ml, 92.9 mmol) was added and the reaction was stirred at 80° C. overnight. The reaction mixture was evaporated under reduced pressure and a white solid was formed. This solid was washed with water and diethyl ether and dried in the vacuum oven to afford 1.8 g (90% yield) of the title compound. Purity 100%.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customa white solid was formed
  3. washThis solid was washed with water and diethyl ether
  4. customdried in the vacuum oven

Sources & evidence

ORD record
ord-c5dec2be34f44a01b83b9a791a8ab349
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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