Acetic Acid → N-Benzyl-4-methyl-2-nitroaniline

HRID 1822152Notes

Reaction equation

HRID 1822152 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[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:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[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 69784-Methyl-2-nitroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15256882N-Benzyl-4-methyl-2-nitroanilineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-2-nitro-phenylamine (202 mg, 1.33 mmol) and benzaldehyde (0.68 mL, 6.65 mmol) in 5 mL dry dichloromethane at room temperature, was added sodium triacetoxyborohydride (282 mg, 1.33 mmol). Then acetic acid (76 μl, 1.33 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. 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 300 mg (1.24 mmol, 94%) of benzyl-(4-methyl-2-nitro-phenyl)-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-0764894d6ef64074b98fe93bf2188e31
Source dataset
uspto-grants-2009_10
Patent number
US07608723B2

Reaction notes

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