Acetyl chloride → 4-Acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline
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
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
100 g (0.55 mol) of 6-chloro-3,4-dihydro-2(1H)-naphthalenone are dissolved under argon in 2 l of toluene, treated with 64.0 g of powdered potassium hydroxide, heated to boiling temperature, 165 g of 3-chloropropylamine hydrochloride are added portionwise thereto during 30 minutes and the mixture is boiled on a water separator until educt can no longer be detected in the thin-layer chromatogram. After cooling to room temperature, the mixture is treated with 155 ml of triethylamine. While cooling with ice so that an internal temperature of 25° is not exceeded, the mixture is treated dropwise with 60 ml of acetyl chloride dissolved in 450 ml of toluene. The mixture is stirred at room temperature for 1 hour, extracted with water/methylene chloride and dried with magnesium sulfate. The solvent is distilled in a vacuum and there is obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in the form of brown crystals which can be used as the crude product for the reaction described hereinafter.
Workup
- temperatureheated
- additionare added portionwise
- temperatureWhile cooling with ice so that an internal temperature of 25°
- extractionextracted with water/methylene chloride
- dry with materialdried with magnesium sulfate
- distillationThe solvent is distilled in a vacuum
Sources & evidence
- ORD record
- ord-56a57c65e3004b24bca192143de8eab6
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04883815
Reaction notes
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