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

HRID 515209Notes

Reaction equation

HRID 515209 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.O1CCOCC1.[CH3:18][NH2:19].CO>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:19][CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 312751,4-DioxaneHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 4-bromo-2-fluoro-1-nitrobenzene (11.8 g, 53.7 mmol), anhydrous 1,4 Dioxane (100 mL), and a 2.0 M solution of methyl amine in methanol (56.4 mL, 113 mmol). The reaction mixture was then heated to 90° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 3.5 hours. The crude reaction mixture was then allowed to cool to room temperature, and concentrated to give 5-bromo-N-methyl-2-nitroaniline (1-1). MS (M)+: observed=230.9, calculated=231.05.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe crude reaction mixture
  4. temperatureto cool to room temperature
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54e72e7a4f734afcb1bedba195b35b5c
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

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