Water → 4-Acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline
Reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][NH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24].O>C(Cl)Cl.CCOCC>[C:23]([N:10]1[C:11]2[CH2:12][CH2:13][C:4]3[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:5]=3[C:6]=2[CH2:7][CH2:8][CH2:9]1)(=[O:25])[CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
229 g (1.04 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline are dissolved in 2 ml of methylene chloride, treated with 115 g (1.14 mol) of triethylamine and 89.5 g (1.14 mol) of acetyl chloride in 400 ml of methylene chloride are added dropwise thereto at 0°. After stirring at room temperature for 1 hour, the mixture is poured into water, extracted with methylene chloride and the methylene chloride phase is dried with magnesium sulfate. Distillation of the solvent in a vacuum gives a crude product which is suspended in 500 ml of ether and removed by filtration. There is obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline with melting point 106°-108°. Concentration of the mother liquor and chromatography (silica gel/chloroform) gives an additional portion with melting point 106°-108°.
Workup
- additionare added dropwise
- customat 0°
- extractionextracted with methylene chloride
- dry with materialthe methylene chloride phase is dried with magnesium sulfate
- distillationDistillation of the solvent in a vacuum
- customgives a crude product which
- customremoved by filtration
Sources & evidence
- ORD record
- ord-dfd9d0f4054f482a8da0039530fb297d
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04883815
Reaction notes
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