HCID 17897329, compound → 5-Chloro-3,4-difluoro-1,2-benzenediamine

HRID 2227186Notes

Reaction equation

HRID 2227186 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([F:12])[C:3]=1[F:13].[H][H]>[Ni].C(O)C>[Cl:1][C:2]1[C:3]([F:13])=[C:4]([F:12])[C:5]([NH2:6])=[C:7]([NH2:9])[CH:8]=1

Participants

5

Reactant 2

HCID 17897329HCID 17897329, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 184721145-Chloro-3,4-difluoro-1,2-benzenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4-Chloro-2,3-difluoro-6-nitroaniline (11.4 g, 54.4. mmol), Raney nickel (Aldrich, Milwaukee, slurry in water, 2.2 g wet) and ethanol (200 mL) were combined in a stirred Parr reactor which was pressurized with hydrogen (250 psig). The mixture was allowed to stir at rt overnight, after which time the reactor was depressurized and the mixture was filtered through Celite and the solvents were removed in vacuo. The remaining residue was dissolved in ethyl acetate, dried over magnesium sulfate and the solvents were removed in vacuo to afford a brownish solid (11.6 g, crude weight); 1H NMR (DMSO-d6) δ: 6.43 (d, J=5.7 Hz, 1H, Ar—H), 5.25 (very br s, 4H, overlapping NH2).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customthe solvents were removed in vacuo
  3. dissolutionThe remaining residue was dissolved in ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customthe solvents were removed in vacuo
  6. customto afford a brownish solid (11.6 g

Sources & evidence

ORD record
ord-801404b2f62045549839bc3da3e9e1e8
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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