4-Chlorobenzoyl chloride → 8-Chloro-4-(p-chlorobenzoyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 569657Notes

Reaction equation

HRID 569657 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.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][N:10]([C:21](=[O:22])[C:20]4[CH:24]=[CH:25][C:17]([Cl:16])=[CH:18][CH:19]=4)[C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Product 1

HCID 221654658-Chloro-4-(p-chlorobenzoyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.78 g (40 mmol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline were dissolved in 88 ml of methylene chloride and 7.70 g (44 mmol) of 4-chlorobenzoyl chloride in 60 ml of methylene chloride were added dropwise thereto at 0°. After stirring at room temperature for 1 hour the mixture was extracted with water, dried with magnesium sulphate and the solvent was distilled off in vacuo. Chromatography (silica gel, chloroform-hexane, 2:1) and crystallization (chloroform-hexane) gave 8-chloro-4-(p-chlorobenzoyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline as white crystals of melting point 189°-191°.

Workup

  1. customat 0°
  2. extractionwas extracted with water
  3. dry with materialdried with magnesium sulphate
  4. distillationthe solvent was distilled off in vacuo
  5. customChromatography (silica gel, chloroform-hexane, 2:1) and crystallization (chloroform-hexane)

Sources & evidence

ORD record
ord-08339df8624545e49d74a6d09be4ded6
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

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