Ammonium Chloride → HCID 59450496, compound

HRID 72301Notes

Reaction equation

HRID 72301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([N+:16]([O-])=O)[CH:9]=2)=[C:4]([F:19])[CH:3]=1.[Cl-].[NH4+]>CO.O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([NH2:16])[CH:9]=2)=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 594505064'-Chloro-4-ethyl-2'-fluoro-3-nitrobiphenyl

Product 1

HCID 59450496HCID 59450496, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

4′-chloro-4-ethyl-2′-fluoro-3-nitrobiphenyl (1.795 g, 6.45 mmol) is suspended in a mixture of methanol (20 ml) and water (4 ml). To this mixture is added zinc dust (2.95 g, 45 mmol) and a solution of ammonium chloride (1.04 g, 19 mmol) in water (4 ml), and once the addition is complete the mixture is heated at reflux for 3 hours. The mixture is cooled to room temperature, and filtered through a plug of diatomaceous earth. The filtrate is partitioned between ethyl acetate and water, and the organic extract is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 4′-chloro-4-ethyl-2′-fluorobiphen-3-ylamine (1.546 g), used without further purification in the next step.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered through a plug of diatomaceous earth
  4. customThe filtrate is partitioned between ethyl acetate and water
  5. extractionthe organic extract
  6. washis washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-3f92fc3b7d8d4f5ca8933fd9200f7610
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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