Water → 8-Chloro-4-(phenylacetyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 569653Notes

Reaction equation

HRID 569653 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:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][N:10]([C:23](=[O:24])[CH2:22][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Product 1

HCID 221654888-Chloro-4-(phenylacetyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.00 g (0.032 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline were dissolved in 50 ml of pyridine and 7.42 g (0.048 mol) of phenylacetyl chloride were added dropwise thereto at 0°. After stirring overnight at room temperature the mixture was poured into water, extracted with ethyl acetate, dried with magnesium sulphate and the solvent was distilled off in vacuo. Chromatography (silica gel, chloroform-hexane, 1:1) gave 8-chloro-4-(phenylacetyl)-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in the form of an oil.

Workup

  1. customat 0°
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with magnesium sulphate
  4. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-bbe67e7260a6410393310af314ecdf48
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

Loading…