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

HRID 399550Notes

Reaction equation

HRID 399550 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(Cl)Cl>C(O)C.[Pt]>[NH2:9][C:7]1[CH:8]=[C:2]([Br:1])[C:3]([NH2:4])=[C:5]([Br:12])[CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 132312,6-Dibromo-4-nitroaniline

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

20 g of 2,6-Dibromo-4-nitroaniline are taken up in 250 ml of ethanol, 250 ml of ethyl acetate, 100 ml of dimethylformamide and 90 ml of methylene chloride and, after addition of 3.3 g of 5% moist platinum/active carbon catalyst, hydrogenated at room temperature under 50 psi for one hour. The solvent is then distilled off in a rotary evaporator, and the residue is triturated with diethyl ether, filtered off with suction and washed several times with petroleum ether.

Workup

  1. distillationThe solvent is then distilled off in a rotary evaporator
  2. customthe residue is triturated with diethyl ether
  3. filtrationfiltered off with suction
  4. washwashed several times with petroleum ether

Sources & evidence

ORD record
ord-0ad8c440815246b7b935f8ec8b1a95bf
Source dataset
uspto-grants-1998_10
Patent number
US05821240

Reaction notes

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