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

HRID 1169996Notes

Reaction equation

HRID 1169996 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 equivalent) and SnCl2 (2.2 equivalents) in EtOH was heated at reflux for 3 hours. After this time, the solution was poured onto ice, brought to pH 10 with 2 M 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+), Rt 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-449ee90d987946bb9b468a8a3992a82e
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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