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

HRID 1748334Notes

Reaction equation

HRID 1748334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CN.C[CH2:15][N:16](C(C)C)C(C)C>CS(C)=O.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:16][CH3:15])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 27368364-chloro-N-methyl-2-nitroanilineYield 81.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-1-fluoro-2-nitrobenzene (832 mg, 4.7 mmol) in DMSO (10 mL) is added a 2M solution of methylamine (3.56 mL, 7.1 mmol) in tetrahydrofuran, followed by Hunig's base (1.2 mL, 7.1 mmol). The reaction flask is sealed and heated to 80° C. for 16 h. The reaction is cooled to room temperature and poured over ice water. The resulting solid is isolated by filtration to afford the title compound (713 mg, 81%).

Workup

  1. customThe reaction flask is sealed
  2. temperatureThe reaction is cooled to room temperature
  3. customThe resulting solid is isolated by filtration

Sources & evidence

ORD record
ord-82fca2f2164c4eb1a6e08d0e642c13d3
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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