Ethanol → 5-Bromo-o-toluidine

HRID 380040Notes

Reaction equation

HRID 380040 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Cl-].[NH4+].C(O)C.[OH-].[Na+]>[Fe].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 1235464-Bromo-2-nitrotoluene

Product 1

HCID 27348055-Bromo-o-toluidineYield 102.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A slurry of 5-bromo-2-methylnitrobenzene (3.00 g), iron powder (3.11 g), and ammonium chloride (2.97 g), in 3:1 ethanol : water (50 ml) was heated at reflux temperature for 1 hour. The mixture was poured into 10% aqueous sodium hydroxide and filtered through Celite®. The filtrate was then extracted with ethyl acetate, the extracts washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the subtitle compound as an oil (2.64 g).

Workup

  1. temperatureat reflux temperature for 1 hour
  2. filtrationfiltered through Celite®
  3. extractionThe filtrate was then extracted with ethyl acetate
  4. washthe extracts washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0afe2c257b8f4b8fba79f5c0eb0868fb
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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