Hydrazine hydrate (1:1) → 4-(1H-Pyrazol-1-yl)benzohydrazide

HRID 2388490Notes

Reaction equation

HRID 2388490 reaction equation
[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O.[NH2:18][NH2:19]>CCO>[N:1]1([C:6]2[CH:16]=[CH:15][C:9]([C:10]([NH:18][NH2:19])=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoate

Product 1

HCID 432366724-(1H-Pyrazol-1-yl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(1H-pyrazol-1-yl)benzoate (711 mg, 3.29 mmol) in absolute EtOH (50 mL) was added hydrazine monohydrate (1.6 mL, 32.9 mmol) at room temperature. The reaction mixture was heated to reflux and stirred for 6 d, then concentrated under reduced pressure. The residue was suspended in H2O (30 mL), filtered, washed with H2O (2×20 mL) and EtOH (2×20 mL) to provide the title compound as an off white solid (101 mg, 15%): 1H NMR (400 MHz, CDCl3, δ in ppm) 9.84 (s, 1H), 8.62-8.59 (m, 1H), 7.98-7.90 (m, 4H), 7.81-7.78 (m, 1H), 6.61-6.57 (m, 1H), 4.51 (br d, J=3.3 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. washwashed with H2O (2×20 mL) and EtOH (2×20 mL)

Sources & evidence

ORD record
ord-7a54964f9cae4713a5fbef7332bd29db
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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