Acrylamide → 8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one

HRID 1639356Notes

Reaction equation

HRID 1639356 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:12]1[CH2:16][CH2:15][CH2:14]C1)[CH2:6][CH2:5]2.C(N)(=[O:20])C=C>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3[CH2:14][CH2:15][C:16](=[O:20])[NH:12][C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6579AcrylamideHCID 10444008Pyrrolidine, 1-(6-chloro-3,4-dihydro-2-naphthalenyl)-

Product 1

HCID 104665398-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

701 g (3 mol) of 1-(6-chloro-3,4-dihydro-2-naphthyl)-pyrrolidine and 640 g (19 mol) of acrylamide in 7 ml of ethanol are boiled under reflux for 3 days with the addition of 70 g of Amberlite IR200. The separated solid is removed by filtration, extractively crystallized with dioxane and there is obtained 8-chloro-1,4,5,6-tetrahydrobenzo[f]-quinolin-3(2H)-one with melting point 228°-230° C.

Workup

  1. temperatureunder reflux for 3 days with the addition of 70 g of Amberlite IR200
  2. customThe separated solid is removed by filtration
  3. customextractively crystallized with dioxane

Sources & evidence

ORD record
ord-cc85e2db7142473394fe502977c273ba
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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