Ammonium Chloride → HCID 62534008, compound

HRID 243070Notes

Reaction equation

HRID 243070 reaction equation
[F: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.[Cl-].[NH4+]>CO.O.[Fe]>[F: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 68158272HCID 68158272, compound

Product 1

HCID 62534008HCID 62534008, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(2,3-Difluoro-6-nitro-phenyl)-phenylamine (4.2 g, 16.9 mmol), iron powder (3.8 g, 67.6 mmol), and ammonium chloride (5.2 g, 101.4 mmol) in methanol (60 mL) and water (15 mL) were heated at 90° C. for 3 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to yield the title compound as a red solid (3.7 g, 100%). 1H NMR 400 MHz δ (CDCl3): 7.25-7.16 (2H, m), 6.94-6.82 (2H, m), 6.70-6.64 (2H, m), 6.47 (1H, ddd, J=12.0, 6.1, 3.0 Hz), 5.23 (1H, br s), 3.71 (2H, br s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with EtOAc (3×40 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95cbadc541cb4f10a1ab07135a741b04
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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