Hydrochloric Acid → HCID 11107389, compound

HRID 1862484Notes

Reaction equation

HRID 1862484 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([F:8])=[N:6][CH:7]=1.C(O)C.Cl>[Fe].O>[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([F:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15142952-Fluoro-5-iodo-3-nitropyridine

Product 1

HCID 11107389HCID 11107389, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Iodo-3-nitro-2-fluoropyridine (1.739 g, 6.49 mmol), ethanol (13 mL), water (2 mL), and concentrated HCl (0.20 mL) were added to a 25 mL round bottom flask and allowed to stir. Iron (3.6 g, 64.4 mmol) was added in portions to the reaction followed by heating at 80° C. for 30 min. The iron was then removed and washed with ethanol over a fritted filter while the ethanol washings were concentrated under reduced pressure. The residue was purified by flash chromatography using 1:2 hexane:ethyl acetate as eluent to give 5-Iodo-2-fluoro-3-aminopyridine as a colorless solid (53%, 0.821 g).

Workup

  1. customThe iron was then removed
  2. washwashed with ethanol over a fritted filter while the ethanol washings
  3. concentrationwere concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ad11efefcb7640c383950108474e1ed5
Source dataset
uspto-grants-2003_03
Patent number
US06538010B1

Reaction notes

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