4-Amino-2-chlorobenzonitrile → 4-amino-2-chloro-5-iodobenzonitrile

HRID 1431711Notes

Reaction equation

HRID 1431711 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[I:11]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[C:9]([I:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1

Participants

4

Reactant 2

HCID 887284-Amino-2-chlorobenzonitrileHCID 120273N-Iodosuccinimide

Product 1

HCID 109128704-amino-2-chloro-5-iodobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-amino-2-chlorobenzonitrile (5.0 g, 33 mmol) and N-iodosuccinimide (8.4 g, 37 mmol) in Acetic Acid (35 mL) was stirred at 23° C. After 18 h, the solid was collected by filtration then purified on silica gel (0-20% EtOAc in hexanes) to afford a pale brown solid as 4-amino-2-chloro-5-iodobenzonitrile. 1H NMR (500 MHz, CDCl3) δ ppm 7.87 (1H, s), 6.77 (1H, s), 4.72 (2H, br. s.)

Workup

  1. filtrationthe solid was collected by filtration
  2. customthen purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2d7e19df3d5147a3a0c8b1d597f7a4b1
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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