Ammonium Chloride → HCID 68157124, compound

HRID 242927Notes

Reaction equation

HRID 242927 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>CO.O.[Fe]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68157998(2-Bromo-3-fluoro-6-nitrophenyl)phenylamine

Product 1

HCID 68157124HCID 68157124, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of (2-bromo-3-fluoro-6-nitrophenyl)phenylamine (2.4 g, 7.7 mmol) in MeOH (40 mL) and water (15 mL) were added NH4Cl (2.38 g, 46.3 mmol) and iron powder (1.72 g, 30.9 mmol) and the reaction mixture heated at 90° C. for 1 h. After cooling to RT, the crude mixture was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound (1.95 g, 90%). LCMS (Method C): RT 3.48 min [M+H]+ 281.1/283.1.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe crude mixture was filtered through a pad of Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting residue was partitioned between EtOAc and water
  5. extractionThe aqueous phase was extracted with EtOAc (×3)
  6. washthe combined organic fractions washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de9511ffaa3a48ac96cc73f33a4f97ba
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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