5-Chloro-2-nitroaniline → 5-Chloro-4-iodo-2-nitroaniline
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[I:12]N1C(=O)CCC1=O>CC(O)=O>[Cl:1][C:2]1[C:3]([I:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 5-chloro-2-nitroaniline (25 g, 145 mmol) in AcOH (250 mL) was added N-iodosuccinimide (32.6 g 145 mmol). The mixture was stirred overnight at 50° C., cooled to rt and filtered. The solid residue was washed with AcOH, water, saturated aqueous NaHCO3 and water, and then dried to afford the desired product as a brown solid, which was used in the next step without further purification.
Workup
- temperaturecooled to rt
- filtrationfiltered
- washThe solid residue was washed with AcOH, water, saturated aqueous NaHCO3 and water
- customdried
Sources & evidence
- ORD record
- ord-3a4a5c46935645c2bfef6cbc54e0077c
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329914B2
Reaction notes
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