Acetyl chloride → 4-Acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 569651

반응식

HRID 569651 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[OH-].[K+].Cl.Cl[CH2:17][CH2:18][CH2:19][NH2:20].[C:21](Cl)(=[O:23])[CH3:22]>C1(C)C=CC=CC=1.C(N(CC)CC)C.O>[C:21]([N:20]1[C:7]2[CH2:6][CH2:5][C:4]3[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=3[C:8]=2[CH2:17][CH2:18][CH2:19]1)(=[O:23])[CH3:22]

참가 물질

8

반응물 4

HCID 6367Acetyl chlorideHCID 14797Potassium HydroxideHCID 44561396-Chloro-2-tetraloneHCID 114690951-Propanamine, 3-chloro-, hydrochloride

생성물 1

HCID 198331194-Acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 8471Triethylamine용매

실험 절차

100 g (0.55 mol) of 6-chloro-3,4-dihydro-2(1H)-naphthalenone were dissolved in 2 l of toluene under argon, treated with 64.0 g of powdered potassium hydroxide, heated to boiling temperature, 165 g of 3-chloropropylamine hydrochloride were added portionwise thereto during 30 minutes and the mixture was boiled on a water separator until educt can no longer be detected in a thin-layer chromatogram. After cooling to room temperature the mixture was treated with 155 ml of triethylamine. The mixture was treated dropwise with 60 ml of acetyl chloride dissolved in 450 ml of toluene while cooling with ice so that an internal temperature of 25° was not exceeded. The mixture was stirred at room temperature for 1 hour, extracted with water/methylene chloride, dried with magnesium sulphate, the solvent was distilled off in vacuo and there was obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in the form of brown crystals which can be employed as the crude product for the reaction described hereinafter.

후처리

  1. temperatureheated
  2. additionwere added portionwise
  3. temperaturewhile cooling with ice so that an internal temperature of 25°
  4. extractionextracted with water/methylene chloride
  5. dry with materialdried with magnesium sulphate
  6. distillationthe solvent was distilled off in vacuo

출처 및 근거

ORD 기록
ord-c7fc9ef211134df49f8793ce57eb19c2
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04732979

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