p-Toluenesulfonic acid → 8-bromo-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one

HRID 579879Notes

Reaction equation

HRID 579879 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23](N1CCCC1)[CH2:22][CH2:21]2>C(Cl)(Cl)Cl>[Br:17][C:18]1[CH:27]=[CH:26][C:25]2[C:24]3[CH2:3][CH2:2][C:1](=[O:4])[NH:5][C:23]=3[CH2:22][CH2:21][C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6579AcrylamideHCID 221654851-(6-Bromo-3,4-dihydronaphthalen-2-yl)pyrrolidine

Product 1

HCID 197073228-bromo-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17.5 g of acrylamide and 0.65 g of p-toluenesulphonic acid were added to 35.5 g of 1-(6-bromo-3,4-dihydro-2-naphthyl)pyrrolidine. The mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours. The reaction mixture was treated with 250 ml of chloroform, whereupon the insoluble constituents were filtered off. There was obtained 8-bromo-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one of melting point 227°-228°. After recrystallization from ethanol the product exhibits a melting point of 230°-231°.

Workup

  1. temperatureThe mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours
  2. filtrationwere filtered off

Sources & evidence

ORD record
ord-44ddbcd326694f0f9058422d22148b8e
Source dataset
uspto-grants-1988_06
Patent number
US04749791

Reaction notes

Loading…