Ammonium Chloride → HCID 86663960, compound

HRID 712171Notes

Reaction equation

HRID 712171 reaction equation
[Br:1][C:2]1[C:3]([F:18])=[C:4]([N+:15]([O-])=O)[C:5]([I:14])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[NH4+].[Cl-]>CO.[Fe]>[Br:1][C:2]1[C:3]([F:18])=[C:4]([C:5]([I:14])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1)[NH2:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86663961HCID 86663961, compound

Product 1

HCID 86663960HCID 86663960, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(5-bromo-4-fluoro-2-iodo-3-nitrophenyl)pyridine (1.0 g, 2.36 mmol) in MeOH (25 mL) was added Fe powder (0.66 mL, 11.82 mmol) at 0° C. The mixture was stirred at rt for 10 min followed by addition of aqueous solution of NH4Cl (0.63 g, 11.82 mmol). The mixture was then heated up to 80° C. for 2 h. After completion of reaction (by TLC), the mixture was poured onto 100 mL of ice cold water and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and solvent evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 6% EtOAc:hexane to obtain the desired product as a white solid (0.90 g, 97%).

Workup

  1. temperatureThe mixture was then heated up to 80° C. for 2 h
  2. customAfter completion of reaction (by TLC)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4 and solvent
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-bb2c82ada2334a169b06378f9bc459c7
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…