N-Benzyl-4-methyl-2-nitroaniline → N-Benzyl-4-methyl-o-phenylenediamine

HRID 1822153Notes

Reaction equation

HRID 1822153 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Fe]>[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15256882N-Benzyl-4-methyl-2-nitroaniline

Product 1

HCID 10727275N-Benzyl-4-methyl-o-phenylenediamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of benzyl-(4-methyl-2-nitro-phenyl)-amine (300 mg, 1.24 mmol) in 5 mL acetic acid, was added iron (300 mg, 1.24 mmol). The reaction mixture was heated to 40° C. under argon for 2 h. The mixture was cooled to ambient temperature and filtered through celite and the filtrate was concentrated. The resulting solid was dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered and the filtrate was concentrated in vacuo to yield crude product that was used in step 3.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe resulting solid was dissolved in ethyl acetate
  5. washThe organic layer was washed with saturated NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customto yield crude product that

Sources & evidence

ORD record
ord-1356b8e31ea040459280d349d8367ec7
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

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