p-Aminoacetophenone → HCID 23323144, compound

HRID 280033Notes

Reaction equation

HRID 280033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)=O>CCOCC>[ClH:1].[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH2:10])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7468p-AminoacetophenoneHCID 178478191HCID 178478191, compound

Product 1

HCID 23323144HCID 23323144, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 400 ml of ethyl ether containing 0.5 mole of 4-chlorophenylmagnesium bromide was added over 1 hour to a mixture of 13.5 g of 4-aminoacetophenone in 500 ml of ether under nitrogen. After heating at reflux for 3 hours, the cooled mixture was quenched with 250 ml of saturated ammonium chloride solution. The dried ethereal layer was evaporated. The residual oil was mixed with 250 ml of 3N hydrochloric acid. After heating on the steam bath for 3 hours, the cooled mixture was separated from a soft solid. The product was taken up in 100 ml of ethanol. Ether (600 ml) was added to give a solid, 14.3 g of 1-(4-aminophenyl)-1-phenylethylene hydrochloride, m.p. 181°-183°.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3 hours
  3. customthe cooled mixture was quenched with 250 ml of saturated ammonium chloride solution
  4. customThe dried ethereal layer was evaporated
  5. additionThe residual oil was mixed with 250 ml of 3N hydrochloric acid
  6. temperatureAfter heating on the steam bath for 3 hours
  7. customthe cooled mixture was separated from a soft solid
  8. additionEther (600 ml) was added

Sources & evidence

ORD record
ord-a935b9a10d7a4fd596950fa5009adec0
Source dataset
uspto-grants-1986_05
Patent number
US04587361

Reaction notes

Loading…