Hydrochloric Acid → 2-Chloro-5-iodo-3-nitropyridine

HRID 1862479Notes

Reaction equation

HRID 1862479 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](N)=[N:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[ClH:18]>Cl[Cu]>[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:18])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 33844682-Amino-5-iodo-3-nitropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 15142942-Chloro-5-iodo-3-nitropyridineYield 36%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

5-iodo-3-nitro-2-aminopyridine (2.511 g, 9.48 mmol) and concentrated HCl (20 mL) were stirred at room temperature for ten minutes. Sodium nitrite (13 g, 188 mmol) was then slowly added followed by CuCl (1.0 g, 10 mmol). Stirring continued overnight. The mixture was poured into 1:1 NH4OH:H2O, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 9:1 hexane:ethyl acetate to yield 5-iodo-3-nitro-2-chloropyridine (984 mg, 36%) as a colorless solid.

Workup

  1. extractionH2O, extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5ded52f126644e38aa6f5dae3c524c32
Source dataset
uspto-grants-2003_03
Patent number
US06538010B1

Reaction notes

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