1-Chloro-2,4-Dinitrobenzene → N-methyl-2,4-dinitroaniline

HRID 1390360Notes

Reaction equation

HRID 1390360 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[CH3:14][NH2:15].[OH-].[Na+]>O>[CH3:14][NH:15][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 6329MethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 74891N-methyl-2,4-dinitroanilineYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

203.5 Parts of 99.5% 2,4-dinitrochlorobenzene are effectively stirred in 390 parts of water. The beige-coloured suspension is heated to 70° C in the course of 35 minutes, and at aprox. 46° C becomes a light brown emulsion. Then 120 parts by volume of a 41% aqueous solution of methylamine are added dropwise at 85° C bath temperature in the course of half an hour. During the dropwise addition the temperature rises to 88° C. The emulsion solidifies slowly and a thick yellow crust forms on the wall of the flask. Thereafter 103 parts by volume of 30% sodium hydroxide solution are added dropwise in the course of a further hour. The temperature falls to below 81° C. The crust gradually detaches itself from the wall of the flask and a yellow suspension forms. This suspension is heated to 90° C in the course of 15 minutes, stirred for 1 hour at 85° to 90° C, then cooled for 2 hours to 30° C and filtered by suction. As the filter cake still contains some lumps, it is stirred in 305 parts of water in a laboratory mixer, filtered by suction, washed with 1150 parts of water and dried at 60° C in vacuo, affording 193 parts of N-methyl-2,4-dinitro-aniline (97.8% of theory, referred to 2,4-dinitrochlorobenzene). The product has a melting point of 177°-178° C.

Workup

  1. custom46° C
  2. additionDuring the dropwise addition the temperature
  3. customrises to 88° C
  4. customfalls to below 81° C
  5. temperatureThis suspension is heated to 90° C in the course of 15 minutes
  6. temperaturecooled for 2 hours to 30° C
  7. filtrationfiltered by suction
  8. stirringis stirred in 305 parts of water in a laboratory mixer
  9. filtrationfiltered by suction
  10. washwashed with 1150 parts of water
  11. customdried at 60° C in vacuo

Sources & evidence

ORD record
ord-176b74391ca942e8a9f3956cbc905086
Source dataset
uspto-grants-1979_02
Patent number
US04138568

Reaction notes

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