p-Anisoyl chloride → 4-(p-Methoxybenzoyl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 1639365Notes

Reaction equation

HRID 1639365 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.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:10]2[C:11]3[CH2:12][CH2:13][C:4]4[CH:3]=[C:2]([Cl:1])[CH:15]=[CH:14][C:5]=4[C:6]=3[CH2:7][CH2:8][CH2:9]2)=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Product 1

HCID 198331524-(p-Methoxybenzoyl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15.0 g (0.06 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline are dissolved in 150 ml of methylene chloride, treated with 6.68 g (0.066 mol) of triethylamine and 11.2 g (0.066 mol) of p-methoxybenzoyl chloride in 50 ml of methylene chloride are added dropwise thereto at 0°. After stirring at room temperature for 1 hour, the mixture is extracted with water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Crystallization (methylene chloride-ether) gives 4-(p-methoxybenzoyl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo-[f]quinoline as white crystals with melting point 182°-183°.

Workup

  1. additionare added dropwise
  2. customat 0°
  3. extractionthe mixture is extracted with water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent is distilled in a vacuum
  6. customCrystallization (methylene chloride-ether)

Sources & evidence

ORD record
ord-80d8c7bd317a4027a8464109a9d723c5
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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