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

HRID 1430748Notes

Reaction equation

HRID 1430748 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-(4-chlorophenyl)-1-ethyl-2-nitrobenzene (22.6 g, 86 mmol) is suspended in methanol (250 ml) and the reaction mixture is stirred at room temperature. 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 under reduced pressure to remove most of the methanol. The residue is partitioned between ethyl acetate and water and the aqueous phase is re-extracted with ethyl acetate. The organic extracts are combined, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure 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 under reduced pressure
  6. customto remove most of the methanol
  7. customThe residue is partitioned between ethyl acetate and water
  8. extractionthe aqueous phase is re-extracted with ethyl acetate
  9. washwashed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-1d3bc50f86724948ba0a44952c97981d
Source dataset
uspto-grants-2015_01
Patent number
US08940913B2

Reaction notes

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