Sodium Acetate → N'-(4-cyanophenyl)acetohydrazide

HRID 559144Notes

Reaction equation

HRID 559144 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].Cl.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1)#[N:8]>C(O)(=O)C>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH:16][C:1](=[O:4])[CH3:2])=[CH:11][CH:10]=1)#[N:8]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 15229386N'-(4-cyanophenyl)acetohydrazideYield 92.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

2.7 g of sodium acetate are added to a solution of 5 g of 4-cyanophenylhydrazine hydrochloride in 40 ml of acetic acid and the mixture is then heated at 80° C. for 20 hours. The reaction mixture is concentrated under vacuum, the residue is taken up with water, the product is extracted with EtOAc, the organic phase is washed with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated off under vacuum. The residue is triturated in a PE/EtOAc (90/10; v/v) mixture and the precipitate formed is filter-dried. 4.8 g of the expected compound are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe product is extracted with EtOAc
  3. washthe organic phase is washed with a saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is triturated in a PE/EtOAc (90/10; v/v) mixture
  7. customthe precipitate formed
  8. customis filter-dried

Sources & evidence

ORD record
ord-f40fa0cb56094592bbef8b6b30bc48bc
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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