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

HRID 725833Notes

Reaction equation

HRID 725833 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>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

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 132312,6-Dibromo-4-nitroaniline

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-nitro-aniline 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-charcoal (5%), are hydrogenated in a Parr apparatus at room temperature under a hydrogen pressure of 1.5 bar for 1 hour. After cooling, the mixture is filtered, the solvent is distilled off in a rotary evaporator and the residue is purified by column chromatography.

Workup

  1. customare hydrogenated in a Parr apparatus at room temperature under a hydrogen
  2. customfor 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. distillationthe solvent is distilled off in a rotary evaporator
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-8b2f955d9d184db98e857024beb0a8d0
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

Loading…