3,4-Dinitrotoluene → N,5-Dimethyl-2-nitroaniline

HRID 1110814Notes

Reaction equation

HRID 1110814 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-])=O.[CH3:14]N.CO>>[CH3:14][NH:1][C:4]1[CH:5]=[C:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 118833,4-DinitrotolueneHCID 57454252Monomethylamine methanol

Product 1

HCID 10103510N,5-Dimethyl-2-nitroanilineYield 96%

Procedure

A solution of 9.10 g of 3,4-dinitrotoluene in 100 ml of 30% methylamine/methanol was reacted at 150° C. for 6 hours in a sealed tube. The reaction solution was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography (200 g). Elution with ethyl acetate-hexane (1 : 3) gave 7.95 g (96%) of 3-(N-methylamino)-4-nitrotoluene.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washElution with ethyl acetate-hexane (1 : 3)

Sources & evidence

ORD record
ord-33caf0308d0f4857a7d430d71fc7eee5
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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