Hydrochloric Acid → 1-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride

HRID 704565

Reaction equation

HRID 704565 reaction equation
B(Cl)(Cl)[Cl:2].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:12][CH2:13][CH2:14][CH2:15][C:16]#N.[Cl-].[Al+3].[Cl-].[Cl-].Cl.CC[O:25]CC>ClCCCl>[ClH:2].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:16](=[O:25])[CH2:15][CH2:14][CH2:13][Cl:12]

Participants

8

Reactant 6

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 6115AnilineHCID 123364-ChlorobutyronitrileHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of boron trichloride (55 g) in 1,2-dichloroethane (200 ml) at 0° was added dropwise a solution of aniline (39.1 g, 0.42 mol) in 1,2-dichlorolethane (50 ml) maintaining the temperature below 5°. On completion of the addition 4-chlorobutyronitrile (41.4 g, 0.42 mol) and aluminium chloride (53.34 g, 0.42 mol) were added successively and the reaction mixture allowed to warm up to room temperature then heated under reflux for 20 hours. After allowing to cool, 2N hydrochloric acid (100 ml) was added and the reaction mixture heated under reflux for 0.5 hour. The solid obtained was collected by filtration, taken up in water and extracted with chloroform (5×200 ml). The chloroform extracts were combined, washed with dilute base, then water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was dissolved in ether and ethanolic HCl was added, the resulting solid was collected by filtration and dried, 28.5 g. Recrystallization from ethanol/diethyl ether gave the product, m.p. 152-154°

Workup

  1. temperaturemaintaining the temperature below 5°
  2. additionwere added successively
  3. temperaturethen heated
  4. temperatureunder reflux for 20 hours
  5. temperatureto cool
  6. temperaturethe reaction mixture heated
  7. temperatureunder reflux for 0.5 hour
  8. customThe solid obtained
  9. filtrationwas collected by filtration
  10. extractionextracted with chloroform (5×200 ml)
  11. washwashed
  12. additionwith dilute base
  13. dry with materialwater, dried over magnesium sulphate
  14. filtrationfiltered
  15. customevaporated under reduced pressure
  16. customto give an oil
  17. filtrationthe resulting solid was collected by filtration
  18. customdried
  19. customRecrystallization from ethanol/diethyl ether
  20. customgave the product, m.p. 152-154°

Sources & evidence

ORD record
ord-1c5e3f2dfdf149f897471fb4864a7eb5
Source dataset
uspto-grants-1991_01
Patent number
US04988695

Linked notes

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