Hydrochloric Acid → 1-(2-Amino-3-methylphenyl)-4-chlorobutan-1-one hydrochloride

HRID 704569

反応式

HRID 704569 の反応式
B(Cl)(Cl)[Cl:2].[NH2:5][C:6]1[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][CH:11]=1.[Cl:13][CH2:14][CH2:15]CC#N.[Cl-].[Al+3].[Cl-].[Cl-].Cl.C([O:26][CH2:27][CH3:28])C>ClCCCl>[ClH:2].[NH2:5][C:6]1[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][C:11]=1[C:27](=[O:26])[CH2:28][CH2:15][CH2:14][Cl:13]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7242O-ToluidineHCID 123364-ChlorobutyronitrileHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 200727531-(2-Amino-3-methylphenyl)-4-chlorobutan-1-one hydrochloride

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

To a solution of boron trichloride (55 g) in 1,2 dichloroethane at 0° was added dropwise a solution of o-toluidine (45.7 g, 0.426 mol) in 1,2 dichloroethane (50 ml) maintaining the temperature below 5°. On completion of the addition 4-chlorobutyronitrile (41.4 g, 0.426 mol) and aluminium chloride (53.34 g, 0.426 mol) were added successively. The reaction mixture was allowed to warm up to room temperature and stirred for 1.5 hours, then heated under reflux for 20 hours. The reaction mixture was then cooled to room temperature poured onto ice (500 g) and 2N hydrochloric acid (200 ml). The mixture was then heated under reflux for 0.5 hour. The organic layer was separated and the aqueous layer was extracted with chloroform (3×100 ml). The organic extracts were combined, washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was dissolved in diethyl ether and HCl gas bubbled through. The resulting solid was collected by filtration and dried (57 g). Recrystallization from ethanol/diethyl ether gave the title compound, m.p. 148-150°.

後処理

  1. temperaturemaintaining the temperature below 5°
  2. additionwere added successively
  3. temperatureheated
  4. temperatureunder reflux for 20 hours
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. temperatureThe mixture was then heated
  7. temperatureunder reflux for 0.5 hour
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with chloroform (3×100 ml)
  10. washwashed with water
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. customevaporated under reduced pressure
  14. customto give an oil
  15. customHCl gas bubbled through
  16. filtrationThe resulting solid was collected by filtration
  17. customdried (57 g)
  18. customRecrystallization from ethanol/diethyl ether

出典と根拠

ORDレコード
ord-0edf058e4f57498dab7a65785e49ee5e
出典データセット
uspto-grants-1991_01
特許番号
US04988695

関連ノート

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