Stannous Chloride → (2-Bromo-5-nitrophenyl)hydrazine

HRID 2233740Notes

Reaction equation

HRID 2233740 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[N:12]([O-])=O.[Na+].[Sn](Cl)Cl>Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][NH2:12]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 826072-Bromo-5-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 53402499(2-Bromo-5-nitrophenyl)hydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 2-bromo-5-nitro-aniline (5 g) in conc hydrochloric acid (50 ml) at 0° C. was added a solution of sodium nitrite (1.45 g) in water (20 ml). After 1 h, a solution of tin dichloride (8.73 g) in conc hydrochloric acid (15 ml) was added. The reaction was stirred for 30 min at 0° C. and 1 h at room temperature. The resulting solid was filtered off and recrystalised from hot ethanol. Yield 2.9 g.

Workup

  1. filtrationThe resulting solid was filtered off
  2. customrecrystalised from hot ethanol

Sources & evidence

ORD record
ord-579cf4552cf64d90b1508cba0aa5d6a2
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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