Hydrazine → 3-Chloro-4-hydroxybenzohydrazide

HRID 1166712Notes

Reaction equation

HRID 1166712 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5](OC)=[O:6].[NH2:13][NH2:14]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:13][NH2:14])=[O:6]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 109542683-Chloro-4-hydroxybenzohydrazideYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a sample of methyl 3-chloro-4-hydroxybenzoate (2 g) dissolved in ethanol (50 mL) was added hydrazine (1.8 mL). The reaction was refluxed overnight under nitrogen. Upon cooling the reaction vessel, the desired product crystallized out of solution. The white solid was isolated by filtration. Recrystallization from hot ethanol gave the 3-chloro-4-hydroxybenzoic acid hydrazide in 60% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under nitrogen
  2. temperatureUpon cooling the reaction vessel
  3. customthe desired product crystallized out of solution
  4. customThe white solid was isolated by filtration
  5. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-f4ea030593b347ce86eed9e07d505227
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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