Dimethylformamide → 2,6-dibromobenzene-1,4-diamine

HRID 1600677Notes

Reaction equation

HRID 1600677 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([Br:12])[C:3]=1[NH2:4].C(OCC)(=O)C.CN(C)C=O.[H][H]>C(O)C.[Pt]>[NH2:4][C:3]1[C:2]([Br:1])=[CH:8][C:7]([NH2:9])=[CH:6][C:5]=1[Br:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 132312,6-Dibromo-4-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 6533412,6-dibromobenzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

3.0 g of 2,6-dibromo-4-nitroaniline are dissolved in 150 ml of ethanol, 150 ml of ethyl acetate and 30 ml of dimethylformamide and, after addition of 0.5 g of platinum on carbon (5%), hydrogenated under a pressure of 1.5 bar of hydrogen in a Parr apparatus at room temperature for 1 hour. Cooling is followed by filtration, the solvent is distilled off in a rotary evaporator, and the residue is purified by column chromatography.

Workup

  1. temperatureCooling
  2. filtrationis followed by filtration
  3. distillationthe solvent is distilled off in a rotary evaporator
  4. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-b1ee345baeaf4d92a55db75fab27a8a9
Source dataset
uspto-grants-1999_11
Patent number
US05977102

Reaction notes

Loading…