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

HRID 579871Notes

Reaction equation

HRID 579871 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

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

229 g (1.04 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline were 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 were added dropwise thereto at 0°. After stirring at room temperature for 1 hour, the mixture was poured into water, extracted with methylene chloride, and the methylene chloride phase was dried with magnesium sulphate. Distillation of the solvent in vacuo gave a crude product which was suspended in 500 ml of ether and filtered off. There was obtained 4-acetyl-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline of melting point 106°-108°. Concentration of the mother liquor and chromatography (silica gel/chloroform) gave a further portion of melting point 106°-108°.

Workup

  1. additionwere added dropwise
  2. customat 0°
  3. extractionextracted with methylene chloride
  4. dry with materialthe methylene chloride phase was dried with magnesium sulphate
  5. distillationDistillation of the solvent in vacuo
  6. customgave a crude product which
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-08be06274f4d4ed8b9e6f3f6f5f37835
Source dataset
uspto-grants-1988_06
Patent number
US04749791

Reaction notes

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