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

HRID 1964262Notes

Reaction equation

HRID 1964262 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([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:10][NH2:11])[CH:7]=[CH:8][CH:9]=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%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Nitro-phenylamine (27.6 g, 0.2 mol) was dissolved in the mixture of H2O (40 mL) and 37% HCl (40 mL). A solution of NaNO2 (13.8 g, 0.2 mol) in H2O (60 mL) was added to the mixture at 0° C., and then a solution of SnCl2.H2O (135.5 g, 0.6 mol) in 37% HCl (100 mL) was added at that temperature. 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 (27.6 g, 73%).

Workup

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

Sources & evidence

ORD record
ord-ddc900bc1c0744bd92036cd04a9e05a3
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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