3-Bromoaniline → (3-Bromophenyl)hydrazine

HRID 16980

Reaction equation

HRID 16980 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[N:9]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][NH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Procedure

To a solution of 3-bromo-phenylamine (17 g, 0.1 mol) in concentrated HCl (200 mL) was added an aqueous solution (20 mL) of NaNO2 (7 g, 0.1 mol) at 0° C. and the resulting mixture was stirred for 1 h. A solution of SnCl2.2H2O (45 g, 0.2 mmol) in concentrated HCl (500 mL) was then added at 0° C. The reaction solution was stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to give (3-bromo-phenyl)-hydrazine as a white solid, which was used for the next reaction without further purification

Workup

  1. stirringThe reaction solution was stirred for an additional 2 h at RT
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-33674e58e9e147fda1e224ede4ce668d
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Linked notes

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