Ammonia → Benzenamine, 3-bromo-4-methyl-

HRID 468791Notes

Reaction equation

HRID 468791 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:11].O.C(O)C.N>[Fe].C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH3:11])[NH2:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 821892-Bromo-4-nitrotoluene

Product 1

HCID 82187Benzenamine, 3-bromo-4-methyl-Yield 71%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromo-4-nitrotoluene (10.0 g, 46.3 mmol) was added to a mixture of water (60 mL), ethanol (130 mL) and acetic acid (40 mL) under nitrogen. The mixture was heated to 70° C. and iron powder (10.3 g, 185 mmol) was added portionwise. After the mixture was heated at refluxed for 2 hours, it was cooled and aqueous ammonia (34%, 180 mL) was added slowly. The mixture is filtered through celite and the aqueous phase was extracted with ethyl acetate. It was dried over MgSO4, filtered, and solvent was removed to give the product as a brown oil (6.0 g, 71%). LCMS (ESI): M+H=185.8.

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureat refluxed for 2 hours
  3. temperatureit was cooled
  4. filtrationThe mixture is filtered through celite
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialIt was dried over MgSO4
  7. filtrationfiltered
  8. customsolvent was removed

Sources & evidence

ORD record
ord-24365ee043f340539273055979b091de
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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