Hydrochloric Acid → 5-Chloro-2-iodopyridin-3-ol

HRID 611561Notes

Reaction equation

HRID 611561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]([I:15])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 227146035-Chloro-2-iodopyridin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20.3 g (0.157 mol) sample of 5-chloro-3-pyridinol (Aldrich Chemical Co.) and 35 g (0.33 mol) of Na2CO3 were dissolved in 220 mL of H2O. To this solution was added 39.9 g of I2, and the reaction mixture was stirred for 45 minutes. The mixture was then poured slowly into 2 N HCl, and the acidity was adjusted to pH 3. The product was collected by filtration and crystallized from EtOH/ether, affording 23.35 g of title compound: 1H NMR (CDCl3, 300 MHz) δ 5.45 (s, 1H), 8.0 (d, 1H); MS m/z: 256 (M+H)+, 273 (M+NH4)+.

Workup

  1. filtrationThe product was collected by filtration
  2. customcrystallized from EtOH/ether

Sources & evidence

ORD record
ord-9244770ca0964ae9b2ff4130d2bd16ba
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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