N-Iodosuccinimide → 4-Chloro-5-iodopyridin-2-amine

HRID 886102Notes

Reaction equation

HRID 886102 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.C1C(=O)N([I:16])C(=O)C1>CN(C=O)C>[Cl:8][C:6]1[C:5]([I:16])=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 219491214-Chloro-5-iodopyridin-2-amineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-chloropyridine (150 g, 0.78 mol) in DMF (1.5 L) was added NIS (341 g, 1.52 mol) and the reaction mixture stirred at RT for 18 h before being concentrated in vacuo to 300 mL volume. The resultant residue was poured into 10% aqueous sodium thiosulfate solution (1.2 L), stirred for 15 min and the precipitate formed collected by filtration, washed with water then dried at 35° C. in vacuo to give the title compound as a pale brown solid (185 g, 62%). 1H NMR 400 MHz (CDCl3) δ: 8.33 (1H, s), 6.68 (1H, s), 4.52 (2H, s).

Workup

  1. concentrationbefore being concentrated in vacuo to 300 mL volume
  2. additionThe resultant residue was poured into 10% aqueous sodium thiosulfate solution (1.2 L)
  3. stirringstirred for 15 min
  4. customthe precipitate formed
  5. filtrationcollected by filtration
  6. washwashed with water
  7. customthen dried at 35° C. in vacuo

Sources & evidence

ORD record
ord-683ca6d3f8e04d71bcecde1357cef54a
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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