N-Iodosuccinimide → HCID 178510178, compound

HRID 1048740Notes

Reaction equation

HRID 1048740 reaction equation
[I:1]N1C(=O)CCC1=O.[OH:9][C:10]1[N:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13]>CN(C)C=O>[OH:9][C:10]1[N:17]=[CH:16][C:15]([I:1])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 178510022HCID 178510022, compound

Product 1

HCID 178510178HCID 178510178, compoundYield 188%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

9 g (0.5 eq) of N-iodosuccinimide at room temperature is added to a solution of 10 g (83 mmol) of 2-hydroxynicotinonitrile in 150 ml of anhydrous dimethylformamide. The reaction mixture is stirred at 60° C. After 30 minutes of stirring, 9 g (0.5 eq) of N-iodosuccinimide is added and then the reaction mixture is stirred at 60° C. for 5 hours. The solvent is evaporated and the precipitate formed is filtered, rinsed with water and with diethyl ether and then dried under vacuum to yield 18.5 g (90%) of 2-hydroxy-5-iodonicotinonitrile in the form of a beige powder.

Workup

  1. stirringAfter 30 minutes of stirring
  2. stirringthe reaction mixture is stirred at 60° C. for 5 hours
  3. customThe solvent is evaporated
  4. customthe precipitate formed
  5. filtrationis filtered
  6. washrinsed with water and with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-695bb48e8eff4c1e86135091832814a2
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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