Ammonium Chloride → HCID 22117686, compound

HRID 1275688Notes

Reaction equation

HRID 1275688 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:8][CH:7]=1.[Cl-:26].[NH4+]>C(O)C.O.[Fe]>[ClH:26].[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22117703HCID 22117703, compound

Product 1

HCID 22117686HCID 22117686, compoundYield 163%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-[4-(2-fluorobenzyloxy)phenoxy]-2-nitrobenzene (0.65 g, 1.9 mmol) in ethanol (50 ml) were added an iron powder (0.53 g, 9.5 mg-atom) and a solution of ammonium chloride (0.06 g, 1.1 mmol) in water (10 ml), followed by reflux for 3 hours. The insoluble matter was removed by filtration, the solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. After drying, the solvent was again evaporated under reduced pressure, the residue was dissolved in a small amount of ethyl acetate, and 4 N hydrogen chloride-ethyl acetate solution (2 ml) was added, followed by stirring for 30 minutes. The solvent was evaporated under reduced pressure, and crystallization from diethyl ether gave the title compound (0.62 g).

Workup

  1. temperatureby reflux for 3 hours
  2. customThe insoluble matter was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customAfter drying
  6. customthe solvent was again evaporated under reduced pressure
  7. dissolutionthe residue was dissolved in a small amount of ethyl acetate, and 4 N hydrogen chloride-ethyl acetate solution (2 ml)
  8. additionwas added
  9. customThe solvent was evaporated under reduced pressure, and crystallization from diethyl ether

Sources & evidence

ORD record
ord-86fbf24021814bc9acb945ab83ea7de7
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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