Methylamine → 4-Bromo-N-methyl-2-nitroaniline

HRID 628576

Reaction equation

HRID 628576 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][NH2:19]>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:19][CH3:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 2580424-Bromo-N-methyl-2-nitroanilineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Bromo-1-fluoro-2-nitrobenzene (1.50 g, 6.82 mmol) and K2CO3 (1.88 g, 13.6 mmol) were suspended in DCM (7 mL). MeNH2 (40% in H2O, 7 mL) was added slowly and the mixture stirred at room temperature for 4 h. The mixture was diluted with H2O and extracted with DCM (3×40 mL). The combined DCM layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the product as a bright orange solid (1.47 g, 93%).

Workup

  1. extractionextracted with DCM (3×40 mL)
  2. washThe combined DCM layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f156aa1de641dab3f3487b0b92803c
Source dataset
uspto-grants-2016_04
Patent number
US09314456B2

Linked notes

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