Isopropylamine → 5-Bromo-N-isopropyl-2-nitroaniline
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureHeat
- customin a sealed reaction vessel to 117° C. overnight
- concentrationconcentrate under reduced pressure
- customPartition the residue between ethyl acetate and saturated aqueous sodium chloride
- dry with materialdry the organic layer over sodium sulfate
- 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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