p-Toluenesulfonic acid → HCID 22165466, compound

HRID 2352380Notes

Reaction equation

HRID 2352380 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([Cl:28])[CH:27]=1)[CH2:24][CH:23](N1CCCC1)[CH2:22][CH2:21]2>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:17][C:18]1[CH:27]=[C:26]([Cl:28])[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 22165478HCID 22165478, compound

Product 1

HCID 22165466HCID 22165466, compound

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Procedure

16.2 g of acrylamide and 0.9 g of anhydrous p-toluenesulphonic acid were added to 30.6 g of 1-(6,8-dichloro3,4-dihydro-2(1H)-naphthyl)pyrrolidine. The mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours. After cooling, the reaction mixture was stirred at room temperature in 80 ml of a mixture of chloroform-ethyl acetate (1:1). There was obtained 8,10-dichloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one which melts at 212°-214° after recrystallization from ethyl acetate.

Workup

  1. temperatureThe mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-2fa98277eade4b09bc8a5b26b154682c
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

Loading…