Hydrazine hydrate (1:1) → 4-Cyanobenzohydrazide

HRID 1468163Notes

Reaction equation

HRID 1468163 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=1)#[N:5]>CCO>[C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([NH:2][NH2:3])=[O:11])=[CH:8][CH:7]=1)#[N:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70791Methyl 4-cyanobenzoate

Product 1

HCID 4567324-CyanobenzohydrazideYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Add hydrazine monohydrate (5.50 mL, 110 mmol) to a solution of methyl 4-cyanobenzoate (3.30 g, 20.5 mmol) in 20 mL of EtOH. Heat the mixture at 80° C. for 1 h resulting in a solution. Cool the mixture to room temperature, causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with cold EtOH followed by diethyl ether to provide 1.90 g, 58% yield of 4-cyano-benzoic acid hydrazide as a light yellow solid.

Workup

  1. customresulting in a solution
  2. temperatureCool the mixture to room temperature
  3. customto precipitate from solution
  4. customCollect the precipitate
  5. filtrationby filtration
  6. washwash with cold EtOH

Sources & evidence

ORD record
ord-98380ef8a04c48e3a2b7cc30609bec4a
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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