N-benzyl-4-bromo-2-nitroaniline → 2-Benzylamino-5-bromoaniline

HRID 1443630Notes

Reaction equation

HRID 1443630 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br: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]([Br: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 24902949N-benzyl-4-bromo-2-nitroaniline

Product 1

HCID 289029062-Benzylamino-5-bromoaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of benzyl-(4-bromo-2-nitro-phenyl)-amine (276 mg, 0.9 mmol) in 3 ml acetic acid, was added iron (70 mg, 1.2 mmol). The reaction mixture was heated to 40° C. under argon for 2 hours. 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 Example 6c.

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-d6b16224bb4d42a892394ffb8c76c5bd
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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