Hydrazine hydrate (1:1) → 5-Bromo-N1-methylbenzene-1,2-diamine

HRID 1402766Notes

Reaction equation

HRID 1402766 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[NH:7][CH3:8].O.NN>CO.[Ni]>[Br:1][C:2]1[CH:9]=[C:6]([NH:7][CH3:8])[C:5]([NH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

5-bromo-N-methyl-2-nitroaniline (1.5 g) was dissolved in methanol (60 mL) by heating to 80° C. Hydrazine hydrate was added (3.2 mL) followed by Raney Nickel (50% slurry in water, 6 drops) and the reaction mixture was heated to reflux for 1 hour. The reaction mixture was filtered through Celite® and concentrated under reduced pressure, providing 5-bromo-N1-methylbenzene-1,2-diamine as an amber oil. This product was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2fd3c4087934461cbc1ca513299dbb52
Source dataset
uspto-grants-2014_12
Patent number
US08912190B2

Reaction notes

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