Sodium Hydroxide → 2-Amino-5-chloro-3-iodopyridine

HRID 1848959Notes

Reaction equation

HRID 1848959 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.Cl[I:10].[OH-].[Na+]>C(O)(=O)C.O>[Cl:8][C:5]1[CH:6]=[C:7]([I:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24640Iodine chlorideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 110760102-Amino-5-chloro-3-iodopyridineYield 60.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

The solution of 2-amino-5-chloropyridine (10.0 g, 77.8 mmol) potassium acetate (7.63 g, 77.8 mmol) in 100 mL of acetic acid was heated to 85° C. and ClI (12.6 g, 77.8 mmol) in 50 mL of acetic acid was added dropwise. Reaction mixture was kept 2 h at this temperature, diluted with 1 L of water, neutralized with NaOH 1N solution to pH 7 and extracted with ethyl acetate (4×75 mL). Organic fraction were combined, washed with NaHCO3, filtered through celite and evaporated. The residue was subjected to column chromatography on silica (eluent—hexane/ethyl acetate 1/1) providing 5-chloro-3-iodopyridin-2-amine as yellow solid (11.9 g, 60%).

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (4×75 mL)
  3. washwashed with NaHCO3
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-d899a0b07cb64fc7ab9f038cc05de715
Source dataset
uspto-grants-2015_02
Patent number
US08952363B2

Reaction notes

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