Sodium Hydroxide → 4-Bromobenzene-1,2-diamine

HRID 392615Notes

Reaction equation

HRID 392615 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[CH:3]=1.Cl[Sn]Cl.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 3235934-Bromobenzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-2-nitroaniline (1.0 eq) and SnCl2(2.2 eq) in EtOH was heated at reflux for 3 hours. After this time, the solution was poured onto ice, brought to pH 10 with 2M NaOH and extracted with Et2O. The combined organic layers were dried over MgSO4 and concentrated. The resulting brown oil was purified by silica gel chromatography (0-50% EtOAc:hexanes) to provide a light yellow solid. LC/MS m/z 187.1 (MH+), Rf 1.33 minutes.

Workup

  1. temperatureat reflux for 3 hours
  2. additionAfter this time, the solution was poured onto ice
  3. extractionextracted with Et2O
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting brown oil was purified by silica gel chromatography (0-50% EtOAc:hexanes)
  7. customto provide a light yellow solid

Sources & evidence

ORD record
ord-fd0eced62f8c4bd8926f8a9dd1f5aa4c
Source dataset
uspto-grants-2004_10
Patent number
US06800760B2

Reaction notes

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