Ammonium Chloride → HCID 68107858, compound

HRID 243801Notes

Reaction equation

HRID 243801 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:19]([O-])=O)[C:8]([O:17][CH3:18])=[C:9]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:19][C:7]1[C:8]([O:17][CH3:18])=[C:9]([CH:11]([OH:16])[C:12]([F:14])([F:15])[F:13])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68107617HCID 68107617, compound

Product 1

HCID 68107858HCID 68107858, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(5-tert-butyl-2-methoxy-3-nitrophenyl)-2,2,2-trifluoroethanol (0.440 g, 1.43 mmol) in ethanol (4.7 mL) and water (2.3 mL), ammonium chloride (0.230 g, 4.30 mmol) and iron powder (0.240 g, 4.30 mmol) were added, and the resulting mixture was heated to reflux for 15 hours. The temperature of the reaction solution was returned to room temperature, the insoluble materials were filtered through a Celite pad. After evaporating the organic solvent under reduced pressure, the aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was evaporated under reduced pressure to obtain 0.397 g of the crude product containing the captioned compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 15 hours
  3. customwas returned to room temperature
  4. filtrationthe insoluble materials were filtered through a Celite pad
  5. customAfter evaporating the organic solvent under reduced pressure
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washthe organic layer was washed with saturated brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-76ec5275f4104ec99cd4f67974e6c935
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

Loading…