Methylamine → 3-fluoro-N-methyl-2-nitroaniline

HRID 1430417Notes

Reaction equation

HRID 1430417 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:5]=1[N+:11]([O-:13])=[O:12]>CO>[F:3][C:4]1[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 544897393-fluoro-N-methyl-2-nitroanilineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol solution of 40% methyl amine (12.2 mL, 119 mmol) was added dropwise to a methanol solution (39.5 mL) of 2,6-difluoronitrobenzene (7.90 g, 49.7 mmol) under ice cooling, and the mixture was stirred at the same temperature for 0.5 hours, and then stirred at room temperature for 3 hours. The reaction solution was poured into ice water, and precipitated crystals were collected by filtration and washed with water. The resulting crystals were dried at 50° C., thereby obtaining 7.84 g of a red, powdery target compound (yield: 93%).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customThe resulting crystals were dried at 50° C.

Sources & evidence

ORD record
ord-070c022202744f7e972492e62014f902
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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