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

HRID 2352366Notes

Reaction equation

HRID 2352366 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7dccbf05b6dd45b4a8299612a15dcf97
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

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