p-Toluenesulfonic acid → HCID 19833158, compound

HRID 1639373Notes

Reaction equation

HRID 1639373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[CH2:8][C:7](=O)[CH2:6][CH2:5]2.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[CH:8]=[C:7]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 44528536,7-dichloro-2-tetralone

Product 1

HCID 19833158HCID 19833158, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9.00 g (0.042 mol) of 6,7-dichloro-3,4-dihydro-2(1H)-naphthalenone and 0.3 g of p-toluenesulfonic acid are dissolved in 200 ml of pyridine, 3.5 ml (0.042 mol) of pyrrolidine are added dropwise and the mixture is boiled under reflux for 2 hours. Distillation of the solvent in a vacuum, addition of 200 ml of ether and filtering off the crystals formed yields 1-(6,7-dichloro-3,4-dihydro-2naphthyl)pyrrolidine with melting point 141°-142°.

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationDistillation of the solvent
  3. additionin a vacuum, addition of 200 ml of ether
  4. filtrationfiltering off the crystals
  5. customformed

Sources & evidence

ORD record
ord-a7aaa6854d2a43b4b2cb450b6c4f03be
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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