3-Nitroaniline → 3-Nitrophenylhydrazinium(1+) chloride

HRID 1964336Notes

Reaction equation

HRID 1964336 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[N:11]([O-])=O.[Na+].[Cl:15][Sn]Cl.O>O.Cl>[ClH:15].[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][NH2:11])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 74233-NitroanilineHCID 23668193Sodium NitriteHCID 43835034Tin dichloride dihydrate

Product 1

HCID 54642853-Nitrophenylhydrazinium(1+) chlorideYield 73.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Nitroaniline (28 g, 0.20 mol) was dissolved in a mixture of H2O (40 mL) and 37% HCl (40 mL). A solution of NaNO2 (14 g, 0.20 mol) in H2O (60 mL) was added to the mixture at 0° C., and then a solution of SnCl2.H2O (140 g, 0.60 mol) in 37% HCl (100 mL) was added. After stirring at 0° C. for 0.5 h, the insoluble material was isolated by filtration and was washed with water to give (3-nitrophenyl)hydrazine hydrochloride (28 g, 73%).

Workup

  1. customthe insoluble material was isolated by filtration
  2. washwas washed with water

Sources & evidence

ORD record
ord-8c272de3b42f4312aa4a1638be88512c
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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