Water → 5-(4-Chlorophenyl)-2-ethylaniline

HRID 1191537Notes

Reaction equation

HRID 1191537 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)=[CH:4][CH:3]=1.O.[Cl-].[NH4+]>CO.[Zn]>[NH2:16][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:13]=[CH:12][C:11]=1[CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 594459324'-Chloro-4-ethyl-3-nitrobiphenyl

Product 1

HCID 594459455-(4-Chlorophenyl)-2-ethylanilineYield 75.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

4′-Chloro-4-ethyl-3-nitrobiphenyl (22.6 g, 0.086 mol) is suspended in methanol (250 ml) and the reaction mixture is stirred at room temperature. Distilled water (100 ml) is added, followed by zinc dust (39.0 g, 0.60 mol) and ammonium chloride (13.8 g, 0.26 mol) and the mixture is heated to reflux for 1 hour. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth and the filtrate is evaporated in vacuo to remove most of the methanol. The residue is partitioned between ethyl acetate (200 ml) and water and the aqueous phase is re-extracted with ethyl acetate (200 ml). The organic extracts are combined, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to give 3-amino-4′-chloro-4-ethylbiphenyl (15.0 g) as a colourless solid. The product is used directly without further purification in Step 5.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through diatomaceous earth
  5. customthe filtrate is evaporated in vacuo
  6. customto remove most of the methanol
  7. customThe residue is partitioned between ethyl acetate (200 ml) and water
  8. extractionthe aqueous phase is re-extracted with ethyl acetate (200 ml)
  9. washwashed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-3c7cefac35f84a27ad56f2b098476ca7
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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