Ethanol → 3,4-Dichlorobenzene-1,2-diamine

HRID 1532609Notes

Reaction equation

HRID 1532609 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-])=O)[C:3]=1[NH2:4].C(O)C.[H][H]>O.[Ni]>[Cl:1][C:2]1[C:3]([NH2:4])=[C:5]([NH2:10])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 3

HCID 702EthanolHCID 30175542,3-Dichloro-6-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 108450203,4-Dichlorobenzene-1,2-diamineYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

2,3-Dichloro-6-nitroaniline (20.11 g, 97.14 mmol), Raney-nickel (4.78 g of a 50% slurry in water), and ethanol (250 mL) were combined in an autoclave which was pressurized to 150 psig with hydrogen. The resulting reaction mixture was allowed to stir at RT overnight. The mixture was then filtered through a pad of celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to leave a dark brown solid. The solid was slurried and in hexanes and was collected on a Büchner funnel to afford 16.31 g (95%) of a brown solid. MS (EI): m/z 177.0 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe mixture was then filtered through a pad of celite, which
  3. washwas subsequently washed with several portions of methanol
  4. customthe solvents were removed by rotary evaporation
  5. customto leave a dark brown solid
  6. customwas collected on a Büchner funnel

Sources & evidence

ORD record
ord-dd5ca54b22db4b52a74be4e86fda2bfb
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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