5-Chloro-2-nitroaniline → 5-Chloro-4-iodo-2-nitroaniline

HRID 1960127Notes

Reaction equation

HRID 1960127 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>C(O)(=O)C>[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

HCID 742185-Chloro-2-nitroanilineHCID 120273N-Iodosuccinimide

Product 1

HCID 223175485-Chloro-4-iodo-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (20.1 g, 116 mmol) and N-iodosuccinimide (26.2 g, 116 mmol) in 260 mL of acetic acid was heated at 55° C. for 16 h and then cooled in an ice-bath. The resulting yellow solid was collected by filtration and rinsed with acetic acid, water, aqueous NaHCO3 and water, and let stand in air for 2 h to provide 5-chloro-4-iodo-2-nitroaniline 1-5 as a yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 7.23 (s, 1H), 8.32 (s, 1H), 7.57 (s, 2H).

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationThe resulting yellow solid was collected by filtration
  3. washrinsed with acetic acid, water, aqueous NaHCO3 and water

Sources & evidence

ORD record
ord-2154481876214e8595a8e7fd33ba9bfe
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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