2,3-Dichloro-6-nitroaniline → 3,4-Dichlorobenzene-1,2-diamine

HRID 2227176Notes

Reaction equation

HRID 2227176 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].[H][H]>[Ni].C(O)C>[Cl:1][C:2]1[C:3]([NH2:4])=[C:5]([NH2:10])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2,3-Dichloro-6-nitroaniline (20.11 g, 97.14 mmol), Raney nickel (Aldrich, Milwaukee, slurry in water, 4.78 g wet), and ethanol (250 mL) were combined in an autoclave which was presssurized 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 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); 1H NMR (DMSO-d6) δ: 6.60 (d, J=8.3 Hz, 1H, ArH), 6.49 (d, J=8.4 Hz, 1H, ArH), 4.98 (br s, 4H, overlapping NH2).

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-ba6ef61aa216406f9824197773e2a936
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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