Hydrochloric Acid → 3-Amino-2-chloro-5-iodopyridine

HRID 1434638Notes

Reaction equation

HRID 1434638 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([Cl:8])=[N:6][CH:7]=1.Cl>O.[Fe].C(O)C>[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15142942-Chloro-5-iodo-3-nitropyridine

Product 1

HCID 15142963-Amino-2-chloro-5-iodopyridineYield 92.3%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

5-iodo-3-nitro-2-chloropyridine (230 mg, 0.809 mmol), ethanol (1 mL), water (6 drops), and concentrated HCl (0.020 mL) were stirred at room temperature for 10 min. Iron (500 mg, 8.95 mmol) was then added in small portions and the reaction round bottom flask was placed into a 100° C. oil bath for 20 min. The iron was removed by filtration, washed with ethanol, then the combined ethanol layers were concentrated under reduced pressure. The crude residue was purified by flash chromatography using 9:1 hexane:ethyl acetate to give 5-iodo-3-amino-2-chloropyridine (190 mg, 92%) as a colorless solid.

Workup

  1. customwas placed into a 100° C.
  2. customfor 20 min
  3. customThe iron was removed by filtration
  4. washwashed with ethanol
  5. concentrationthe combined ethanol layers were concentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-78318c370442432a80a8d4eed3416906
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Reaction notes

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