Ammonium Chloride → 4-Methoxy-o-phenylenediamine

HRID 1750108Notes

Reaction equation

HRID 1750108 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-])=O)[CH:4]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:7])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 1534044-Methoxy-o-phenylenediamineYield 69%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-methoxy-2-nitroaniline (10 g, 59.4 mmol) in EtOH (200 mL) and water (80 mL) was added iron (12 g, 210 mmol) and ammonium chloride (9.63 g, 180 mmol). The mixture was then heated to reflux and stirred overnight. The mixture was filtered and the filtrate was evaporated to remove the EtOH and the residue was purified by flash chromatography on silica gel column (elution with DCM/MeOH=80:1) to give 4-methoxybenzene-1,2-diamine (intermediate 35) (5.65 g, 69%) as a yellow solid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customto remove the EtOH
  6. customthe residue was purified by flash chromatography on silica gel column (elution with DCM/MeOH=80:1)

Sources & evidence

ORD record
ord-27a9aa6ba4ca446596293614a3b84c5b
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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