Potassium Iodide → 3-Chloro-2-iodo-5-nitropyridine

HRID 2069901Notes

Reaction equation

HRID 2069901 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[I-:12].[K+].C(OCC)(=O)C>C(O)(=O)C>[Cl:8][C:7]1[C:2]([I:12])=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 369954523-Chloro-2-iodo-5-nitropyridineYield 91.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2,3-dichloro-5-nitropyridine (9.75 g) and potassium iodide (29 g) in acetic acid (120 mL, degassed with nitrogen) was heated to 100° C. for 1.5 hours under nitrogen. The brown solution was cooled to room temperature and then ethyl acetate (300 mL) added. The organic phase was separated and washed with water (2×100 mL) and dilute aqueous sodium sulfite (100 mL). Evaporation of the solvent gave crystalline 3-chloro-2-iodo-5-nitro-pyridine (13.11 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (2×100 mL) and dilute aqueous sodium sulfite (100 mL)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a1ff93ae7b8c441ea27f4060e8e0920b
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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