p-Toluenesulfonic acid → HCID 14762160, compound

HRID 2352375Notes

Reaction equation

HRID 2352375 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 14762160HCID 14762160, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

12.0 g of 6-methoxy-2-tetralone were boiled at reflux for 2 hours in 200 ml of benzene and 5.6 ml of pyrrolidine, in the presence of 0.5 g of anhydrous p-toluenesulphonic acid. The toluene was removed in vacuo. 9.70 g of acrylamide and 0.5 g of p-toluenesulphonic acid were added to the thus-obtained crude 1-(6-methoxy-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 partitioned between 400 ml of chloroform and 40 ml of water. The organic phase was washed with 2×40 ml of water and the aqueous phases were extracted with 1×100 ml of chloroform. The chloroform phases were combined, dried over sodium sulphate and concentrated. The residue was chromatographed on 160 g of silica gel (particle size 0.2-0.5 mm). The 8-methoxy-1,4,5,8-tetrahydrobenzo[f]quinolin-3(2H)-one, eluted with methylene chloride and recrystallized from ethyl acetate, exhibits a melting point of 208°-209°.

Workup

  1. customThe toluene was removed in vacuo
  2. addition9.70 g of acrylamide and 0.5 g of p-toluenesulphonic acid were added to the

Sources & evidence

ORD record
ord-2abac64effd04f738b1296e30e8a78e3
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

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