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

HRID 1434637

Reaction equation

HRID 1434637 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-9c8d146798a34822a21c69430887e465
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Linked notes

Loading…