Isopropylamine → 5-Bromo-N-isopropyl-2-nitroaniline

HRID 250728Notes

Reaction equation

HRID 250728 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]([NH2:15])([CH3:14])[CH3:13]>C(O)CCC>[CH:12]([NH:15][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 123156462,4-Dibromo-1-nitrobenzene

Product 1

HCID 249029775-Bromo-N-isopropyl-2-nitroanilineYield 94%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Heat a mixture of 2,4-dibromonitrobenzene (3.50 g, 12.5 mmol), isopropylamine (4.42 g, 6.40 ml, 74.8 mmol) and n-butanol (20 ml) in a sealed reaction vessel to 117° C. overnight. Cool to room temperature and concentrate under reduced pressure. Partition the residue between ethyl acetate and saturated aqueous sodium chloride, dry the organic layer over sodium sulfate, and concentrate under reduced pressure to provide the desired compound as a yellow solid (3.0 g, 94%).

Workup

  1. temperatureHeat
  2. customin a sealed reaction vessel to 117° C. overnight
  3. concentrationconcentrate under reduced pressure
  4. customPartition the residue between ethyl acetate and saturated aqueous sodium chloride
  5. dry with materialdry the organic layer over sodium sulfate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-edab10343770457682b580b83bba213f
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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