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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1748334Generated: October 30, 2026

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

https://huagongshe.com/reaction/1748334

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
Reactant4-Chloro-1-fluoro-2-nitrobenzeneHCID 67660—
ReactantDiisopropylethylamineHCID 81531—
SolventDimethyl SulfoxideHCID 679—
SolventTetrahydrofuranHCID 8028—
Product4-chloro-N-methyl-2-nitroanilineHCID 273683681.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150577B2
Source datasetuspto-grants-2015_10
ORD IDord-82fca2f2164c4eb1a6e08d0e642c13d3
Source noteuspto-grants-2015_10