N-Methylbenzylamine → N-Benzyl-2-fluoro-N-methyl-4-nitroaniline

HRID 2237611Notes

Reaction equation

HRID 2237611 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[CH2:12]([NH:19][CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:12]([N:19]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11])[CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 59302854N-Benzyl-2-fluoro-N-methyl-4-nitroanilineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2-difluoro-4-nitro-benzene (0.96 g, 6.0 mmole) and benzyl methylamine (0.79 g, 6.6 mmole) in 4 mL of anhydrous DMF is heated with K2CO3 (0.41 g, 3.0 mmole) at 80° C. for 16 hours. After removal of the solvent, the residue is purified on flash chromatography with EtOAc/Hexanes (0-15%), yielding yellow oil 1.05 g (4.0 mmole) 67% of benzyl-(2-fluoro-4-nitro-phenyl)-methylamine.

Workup

  1. customAfter removal of the solvent
  2. customthe residue is purified on flash chromatography with EtOAc/Hexanes (0-15%)

Sources & evidence

ORD record
ord-daa3474617cb416eb7d6d5773429612e
Source dataset
uspto-grants-2010_05
Patent number
US07718671B2

Reaction notes

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