ChemicalBook CAS DataBase List Phenylhydrazine hydrochloride

Phenylhydrazine hydrochloride synthesis

8synthesis methods

Product Name:Phenylhydrazine hydrochloride
CAS Number:59-88-1
Molecular formula:C6H9ClN2
Molecular Weight:144.6

62-53-3 Synthesis

62-53-3
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59-88-1
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Yield:59-88-1 98%

Reaction Conditions:

Stage #1:aniline with hydrogenchloride;sodium nitrite in water at 0; for 1 h;
Stage #2: with hydrogenchloride;tin(ll) chloride in water at 20; for 2 h;

Steps:

Phenylhydrazine hydrochloride (9a)
To a solution of aniline (1 equiv., 2.28 mL, 25 mmol) in a mixture of H2O (20 mL) and concentrated HCl (12 M, 12.5 mL), a solution of NaNO2 (1.05 equiv., 1.81 g, 26.3 mmol) in H2O (4 mL) was added dropwise at 0 °C and the reaction mixture was stirred at this temperature for 1 h. Then, a solution of SnCl2 (2 equiv., 9.48 g, 50 mmol) in concentrated HCl (12 M, 15 mL) was added dropwise and the mixture was stirred at room temperature for 2 hours. The precipitate was filtered, washed with brine, Et2O and dried in vacuo at 40 °C overnight. A pale brown solid was obtained corresponding to phenylhydrazine hydrochloride (98percent yield, 3.55 g, 24.5 mmol). The product was used without further purification for the subsequent reaction.

References:

Guillemard, Lucas;Jacob, Nicolas;Wencel-Delord, Joanna [Synthesis,2020,vol. 52,# 4,p. 574 - 580] Location in patent:supporting information

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108-86-1 Synthesis