p-Toluenesulfonic acid → 3-Pyrrolidino-5-chloro-1,2-dihydronaphthalene

HRID 2352358Notes

Reaction equation

HRID 2352358 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 46232698-Chloro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 151372213-Pyrrolidino-5-chloro-1,2-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

70.0 g of 8-chloro-3,4-dihydro-2(1H)-naphthalenone were boiled at reflux for 2.5 hours in 550 ml of benzene and 33 ml of pyrrolidine in the presence of 1.4 g of p-toluenesulphonic acid. The crude 1-(8-chloro-3,4-dihydro-2-naphthyl)-pyrrolidine obtained was processed without purification.

Sources & evidence

ORD record
ord-40b91bf9ee414ad4b93378b3255970fd
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

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