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

HRID 341685Notes

Reaction equation

HRID 341685 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 refluxed 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 refluxed for 2 hours
  2. customThe dioxane is evaporated under reduced pressure
  3. additionThe residue is diluted with water
  4. additionthe solution made basic by addition of 2N aqueous potassium hydroxide solution
  5. extractionextracted with ethyl acetate (3×500 ml)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-833ac59a57cc467d810bd8ae02b19839
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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