Stannous chloride dihydrate → 4-Bromobenzene-1,2-diamine

HRID 2307808Notes

Reaction equation

HRID 2307808 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl>CO.Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 3235934-Bromobenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-2-nitroaniline (1 g; 4.6 mmol) and SnCl2.2H2O (6.2 g; 27.6 mmol) in MeOH (30 mL) with 5-6 drops of conc. HCl was heated at reflux for 5 hrs., concentrated, suspended in sat'd NaHCO3 (aq.) and extracted with EtOAc. The extracts were rinsed with brine, dried (MgSO4), and concentrated to provide the product of sufficient purity to carry on.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hrs
  3. concentration, concentrated
  4. extractionextracted with EtOAc
  5. washThe extracts were rinsed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto provide the product of sufficient purity

Sources & evidence

ORD record
ord-623d46138bf6428293ad7002bf5ab98d
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

Loading…