Hydrochloric Acid → 4'-Chloro-3-ethylbiphen-4-ylamine

HRID 72289Notes

Reaction equation

HRID 72289 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9]([NH:14]C(=O)C)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9]([NH2:14])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59450487N-(4'-chloro-3-ethylbiphen-4-yl)acetamide

Product 1

HCID 594504954'-Chloro-3-ethylbiphen-4-ylamineYield 97.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(4′-chloro-3-ethylbiphen-4-yl)acetamide (18 g, 0.06 mol) in dioxane (126 ml), is added concentrated hydrochloric acid (36 ml) and the reaction mixture is heated at reflux for 2 hours. The dioxane is evaporated under reduced pressure. The residue is diluted with water, the solution made basic by addition of 2N aqueous potassium hydroxide solution and extracted with ethyl acetate (3×500 ml). The organic extracts are combined and concentrated under reduced pressure to give 4′-chloro-3-ethylbiphen-4-ylamine (13.5 g).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. customThe dioxane is evaporated under reduced pressure
  4. additionThe residue is diluted with water
  5. additionthe solution made basic by addition of 2N aqueous potassium hydroxide solution
  6. extractionextracted with ethyl acetate (3×500 ml)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-174230f29d8d42999a762870b73e9c18
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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