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

HRID 475270Notes

Reaction equation

HRID 475270 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>CC(O)=O>[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-iodobenzonitrileYield 39.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-amino-2-chlorobenzonitrile (5.0 g, 0.033 mol) and N-iodosuccinimide (8.28 g, 0.036 mol) in HOAc (35 mL) was stirred at RT overnight. A brown solid formed, which was collected by filtration, washed with hexanes, and dried in vacuo to afford 3.6 g (39%) of 4-amino-2-chloro-5-iodobenzonitrile (236) as a pale brown solid: MS (ESI) m/z=278.8 [M+1]+.

Workup

  1. customA brown solid formed
  2. filtrationwhich was collected by filtration
  3. washwashed with hexanes
  4. customdried in vacuo

Sources & evidence

ORD record
ord-962b652c1b33479792d193053f000dbc
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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