Water → 1-(2-Aminophenyl)-4-chloro-1-butanone

HRID 1654279Notes

Reaction equation

HRID 1654279 reaction equation
B(Cl)(Cl)Cl.[Cl:5][CH2:6][CH2:7][CH2:8][C:9]#N.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH2:22]>ClCCCl>[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:9](=[O:22])[CH2:8][CH2:7][CH2:6][Cl:5]

Participants

7

Reactant 5

HCID 962WaterHCID 6115AnilineHCID 123364-ChlorobutyronitrileHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110525851-(2-Aminophenyl)-4-chloro-1-butanoneYield 89.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of BCl3 (59.2 g, 0.50 mole) in 1,2-dichloroethane is treated with 4-chlorobutyronitrile (62.5 g, 0.604 mole) over a 1 hour period at -8° to 0° C., stirred for 1 hour at 0° to 5° C., treated with aniline (45.1 g, 0.485 mole) over a 1 hour period at 2° to 9° C., stirred for 1 hour, and treated with AlCl3 (68.8 g, 0.515 mole) in a single portion at ambient temperatures. The reaction mixture is sparged with nitrogen at reflux temperature for about 17 hours. The heated and sparged reaction mixture is cooled to 35° C. and added to approximately a 2-fold volume of water (based upon initial reaction volume) and stirred for 0.5 hour at 33° to 35° C. The phases are separated and the aqueous phase is washed with 1,2-dichloroethane. The organic phases are combined and concentrated in vacuo to give a solution of the title product containing, 85.9 g of the desired o-aminophenyl ketone, 89.7% yield, identified by HPLC analysis.

Workup

  1. stirringstirred for 1 hour
  2. customThe reaction mixture is sparged with nitrogen
  3. temperatureat reflux temperature for about 17 hours
  4. temperatureThe heated
  5. customsparged
  6. customreaction mixture
  7. customreaction volume) and
  8. stirringstirred for 0.5 hour at 33° to 35° C
  9. customThe phases are separated
  10. washthe aqueous phase is washed with 1,2-dichloroethane
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c561e96087d45e68625e718ec64af8e
Source dataset
uspto-grants-1995_04
Patent number
US05405998

Reaction notes

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