Isopropylamine → 4-Chloro-2-nitro-N-(propan-2-yl)aniline

HRID 1654474Notes

Reaction equation

HRID 1654474 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]([NH2:15])([CH3:14])[CH3:13]>O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:15][CH:12]([CH3:14])[CH3:13])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 69772,5-Dichloronitrobenzene

Product 1

HCID 27366924-Chloro-2-nitro-N-(propan-2-yl)anilineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,5-Dichloronitrobenzene (150 g) was added to isopropylamine (150 g) and the mixture was stirred in a sealed tube at 100° C. for 4 hours. After cooling, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure to give 4-chloro-N-isopropyl-2-nitroaniline (163 g). A part of the obtained product was recrystallized from methanol, which showed the following physical properties:

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-acca3e9597334039b49c1bb8055f6444
Source dataset
uspto-grants-1995_04
Patent number
US05407936

Reaction notes

Loading…