Hydrazine hydrate (1:1) → 4-Cyanobenzohydrazide

HRID 2388415Notes

Reaction equation

HRID 2388415 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7](OCC)=[O:8])=[CH:5][CH:4]=1)#[N:2].O.[NH2:15][NH2:16]>C(O)C>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([NH:15][NH2:16])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 81589Ethyl 4-cyanobenzoate

Product 1

HCID 4567324-CyanobenzohydrazideYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 250 mL round bottom flask charged with ethyl 4-cyanobenzoate (16.85 g, 96.2 mmol) in 95% ethanol (75 mL) was added hydrazine mono-hydrate (18.2 mL, 64% solution, 240 mmol). This mixture was heated to reflux for a period of 4.5 h, then allowed to cool to room temperature over a 16 h period. The solvent was removed under reduced pressure and the yellow residue was taken up in ice-cold water (150 mL). The light yellow solid was filtered off and washed with additional cold water (50 mL). The solid was then dried under high vacuum to yield the title compound as a light yellow solid (13.98 g, 90%). 1H NMR (400 MHz, DMSO-d6, δ in ppm) 10.05 (br s, 1H), 7.95 (AA′XX′, J=8.5 Hz, 4H), 4.61 (br s, 2H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for a period of 4.5 h
  3. customThe solvent was removed under reduced pressure
  4. filtrationThe light yellow solid was filtered off
  5. washwashed with additional cold water (50 mL)
  6. customThe solid was then dried under high vacuum

Sources & evidence

ORD record
ord-52dde1a301114cf58c083424386a9602
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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