Ammonium Chloride → HCID 22033543, compound

HRID 325028Notes

Reaction equation

HRID 325028 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:5]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22033514Nitro-3-[2-(4-cyanophenyl)ethoxy]benzene

Product 1

HCID 22033543HCID 22033543, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Nitro-3-[2-(4-cyanophenyl)ethoxy]benzene (3.0 g; 11.2 mmol; from step (i) above) and NH4Cl (2.9 g; 55 mmol) were dissolved in a mixture of EtOH (40 mL) and H2O (10 mL) and heated to reflux. Iron powder (3.0 g; 55 mmol) was added and heating was continued for 1 hour. The mixture was filtered, concentrated in vacuo and partitioned between water and CH2Cl2. After separation, the aqueous phase was extracted with CH2Cl2. The combined organic phases were dried (MgSO4) and the solvent was evaporated. Purification by flash chromatography (SiO2; toluene:EtOAc (9:1)) afforded 2.26 g (85%) of the sub-title compound.

Workup

  1. temperatureheated to reflux
  2. temperatureheating
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. custompartitioned between water and CH2Cl2
  6. customAfter separation
  7. extractionthe aqueous phase was extracted with CH2Cl2
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. customthe solvent was evaporated
  10. customPurification by flash chromatography (SiO2; toluene:EtOAc (9:1))

Sources & evidence

ORD record
ord-8ef99bd1e03243c586593e9f31e39f13
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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