Ammonium Chloride → HCID 23155082, compound

HRID 1912795Notes

Reaction equation

HRID 1912795 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Cl-].[NH4+]>C(O)C.O.[Zn]>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][OH:9])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 23155082HCID 23155082, compoundYield 124.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In 21 mL of ethanol, 4.51 g (20 mmol) of 2-chloro-5-nitrobenzotrifluoride was dissolved, and a solution obtained by dissolving 3.8 g of zinc powder and 420 mg of ammonium chloride in 5 mL of water was added thereto, and the mixture solution was stirred at 70° C. for one hour. The reaction solution after removal of insolubles by filtration was concentrated, and the residue was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried, and then concentrated under reduced pressure, and to the obtained residue, 30 mL of a 4N hydrogen chloride ethyl acetate solution was added, and the formed white precipitate was collected by filtration, washed with ethyl acetate and vacuum dried to obtain 3.08 g (63%) of N-(4-chloro-3-(trifluoromethyl)phenyl)hydroxylamine hydrochloride.

Workup

  1. customa solution obtained
  2. additionwas added
  3. customThe reaction solution after removal of insolubles
  4. filtrationby filtration
  5. concentrationwas concentrated
  6. customthe residue was partitioned between water and ethyl acetate
  7. washthe organic layer was washed with a saturated sodium chloride solution
  8. customThe organic layer was dried
  9. concentrationconcentrated under reduced pressure
  10. additionto the obtained residue, 30 mL of a 4N hydrogen chloride ethyl acetate solution was added
  11. filtrationthe formed white precipitate was collected by filtration
  12. washwashed with ethyl acetate and vacuum
  13. customdried

Sources & evidence

ORD record
ord-512e2c18ec134e4fabeeb3f506cd8797
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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