Hydrochloric Acid → 2,3-Dichloro-5-iodopyridine

HRID 1434639Notes

Reaction equation

HRID 1434639 reaction equation
[I:1][C:2]1[CH:3]=[C:4](N)[C:5]([Cl:8])=[N:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[ClH:16]>Cl[Cu]>[Cl:8][C:5]1[C:4]([Cl:16])=[CH:3][C:2]([I:1])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 15142963-Amino-2-chloro-5-iodopyridineHCID 23668193Sodium Nitrite

Product 1

HCID 218928742,3-Dichloro-5-iodopyridineYield 70%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

5-iodo-3-amino-2-chloropyridine (1.212 g, 4.76 mmol) and concentrated HCl (10 mL) were stirred at room temperature for ten minutes. Sodium nitrite (5.3 g, 76.8 mmol) was then slowly added followed by CuCl (4.0 g, 40.4 mmol). Stirring continued for 30 min. 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 95:5 hexane:ethyl acetate to yield 2,3-Dichloro-5-iodopyridine (913 mg, 70%) 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-d3b5cde3d97b468489596abf692c9a18
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Reaction notes

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