Iodine → HCID 178510339, compound

HRID 506172Notes

Reaction equation

HRID 506172 reaction equation
[OH:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[I:10]I.[OH-].[Na+]>O>[OH:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[I:10]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 178510337HCID 178510337, compound

Product 1

HCID 178510339HCID 178510339, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 4-hydroxynicotinonitrile (45.7 g, 381 mmol), iodine (96.6 g, 381 mmol) and NaOH (19.8 g, 825 mmol) in water (600 mL) was heated at 85° C. overnight, cooled to r.t. and diluted with water. The precipitate was collected by filtration and washed with water to give 57.5 g (61%) of 4-hydroxy-5-iodonicotinonitrile as a tan solid. Mp>245° C.

Workup

  1. temperaturecooled to r.t.
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-a88d4654205b49ecac2b716b56ed3020
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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