Water → 5-Chloro-2-methylaniline

HRID 1439913Notes

Reaction equation

HRID 1439913 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH3:11])([O-])=O.O>CO.[Fe]>[NH2:1][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH3:11]

Participants

5

Reactant 2

HCID 962WaterHCID 6975Benzene, 4-chloro-1-methyl-2-nitro-

Product 1

HCID 72605-Chloro-2-methylanilineYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-4-chlorotoluene (86 g, 0.5 mol) in MeOH (250 mL) was added Fe powder (92 g, 3.65 mol) by portions over 45 min while refluxing gently. The mixture was stirred for 3 h at room temperature, poured into water (1.5 L) and extracted with AcOEt. The organic layers were dried over MgSO4 and concentrated in vacuo to give 63 g of the title compound.

Workup

  1. temperaturewhile refluxing gently
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56ebfbf913674fd4b595f3908f059b0b
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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