Methylamine → 5-bromo-N-methyl-2-nitroaniline

HRID 2037807Notes

Reaction equation

HRID 2037807 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([NH:2][CH3:1])[CH:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 106095305-bromo-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylamine (2 M in tetrahydrofuran, 11.4 mL) was added to a mixture of 4-bromo-2-fluoro-1-nitro-benzene (2.50 g) and K2CO3 (1.90 g) in dimethylformamide (40 mL). The resulting mixture was stirred at ambient temperature overnight. Then, the mixture was concentrated under reduced pressure and dichloromethane was added. The resulting mixture was washed with 0.5 M aqueous HCl solution and brine and dried (MgSO4). The solvent was removed to give the product as a solid.

Workup

  1. concentrationThen, the mixture was concentrated under reduced pressure and dichloromethane
  2. additionwas added
  3. washThe resulting mixture was washed with 0.5 M aqueous HCl solution and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e07046d4984840bbbb9ce4011ae3e8bb
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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