Iodine → HCID 21104779, compound

HRID 1354241Notes

Reaction equation

HRID 1354241 reaction equation
[I:1]I.[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C([O-])([O-])=O.[Na+].[Na+]>>[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([I:1])=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 807Iodine2×HCID 10340Sodium CarbonateHCID 811362-Chloro-3-pyridinol

Product 1

HCID 21104779HCID 21104779, compound

Procedure

I2 (45.8 g, 0.18 mol) is added to a solution of 2-chloro-3-pyridinol (69, 23.4 g, 0.18 mol) in Na2CO3 (225 ml, 1.0M aqueous solution, 0.225 mol). The I2 initially remains in the bottom of the flask but dissolves with stirring overnight. The solution becomes lighter in color dark and a white solid precipitates. The mixture is then diluted with EtOAc and acidified with concentrated HCl to pH 2–3. The solution is extracted with EtOAc. The combined extracts are washed with H2O, dried, evaporated to give the 2-chloro-5-iodo-3-pyridinol as a yellow solid.

Workup

  1. dissolutiondissolves
  2. customa white solid precipitates
  3. additionThe mixture is then diluted with EtOAc
  4. extractionThe solution is extracted with EtOAc
  5. washThe combined extracts are washed with H2O
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d123d1214689414fb7afafe175ee34c1
Source dataset
uspto-grants-2007_05
Patent number
US07223778B2

Reaction notes

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