p-Toluenesulfonic acid → HCID 22165459, compound

HRID 579881Notes

Reaction equation

HRID 579881 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=O)[CH2:7]2.N1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:29]([NH2:33])(=[O:32])[CH:30]=[CH2:31]>C1C=CC=CC=1.O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[CH2:4][CH2:5][C:6]3[NH:33][C:29](=[O:32])[CH2:30][CH2:31][C:7]=3[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acid2×HCID 6579AcrylamideHCID 31268PyrrolidineHCID 35627545-Chloro-2-Tetralone

Product 1

HCID 22165459HCID 22165459, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

11.07 g of 5-chloro-2-tetralone were boiled at reflux for 2 hours in 200 ml of benzene and 10.1 ml of pyrrolidine in the presence of 0.3 g of p-toluenesulphonic acid. The crude 1-(5-chloro-3,4-dihydro-2-naphthyl)pyrrolidine obtained was treated, without purification, with 9.0 g of acrylamide and 0.5 g of p-toluenesulphonic acid. The mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours. 250 ml of ethyl acetate and 50 ml of water were added to the reaction mixture, whereupon the insoluble constituents were filtered off, washed with ethyl acetate and water, dried and recrystallized from ethyl acetate. There was obtained 7-chloro-1,2,5,6-tetrahydrobenzo[f]quinolin-3(4H)-one of melting point 252°-253°.

Workup

  1. customThe crude 1-(5-chloro-3,4-dihydro-2-naphthyl)pyrrolidine obtained
  2. temperatureThe mixture was heated under nitrogen to 100° for 2 hours and to 150° for 2 hours
  3. filtrationwere filtered off
  4. washwashed with ethyl acetate and water
  5. customdried
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8fa7a6d54614cbeb744bd60e337408f
Source dataset
uspto-grants-1988_06
Patent number
US04749791

Reaction notes

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