Acetic Acid → N-benzyl-4-bromo-2-nitroaniline

HRID 1443629Notes

Reaction equation

HRID 1443629 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH2:12]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 701324-Bromo-2-nitroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 24902949N-benzyl-4-bromo-2-nitroanilineYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Bromo-2-nitroaniline (435 mg, 2 mmol) and benzaldehyde (0.204 ml, 2 mmol,) in 4 ml dry dichloromethane at room temperature, was added sodium triacetoxyborohydride (424 mg, 2 mmol). Then acetic acid (120 μl, 2 mmol) was added. The reaction mixture was stirred at room temperature for 8 hours. The solvent was evaporated and the solid was dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered, and the solvent was removed in vacuo. The crude material was purified by flash chromatography to yield 276 mg (0.9 mmol, 45%) of benzyl-(4-bromo-2-nitrophenyl)-amine.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe solid was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-e0c95a70d11d48ddbf748810220b2aca
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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