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

HRID 2352368Notes

Reaction equation

HRID 2352368 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-b0228d4a7efd49858952b84819a442ee
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

Loading…