p-Toluenesulfonic acid → 2-Benzylamino-5,8-dimethoxy-3,4-dihydronaphthalene

HRID 128712Notes

Reaction equation

HRID 128712 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH2:8]2.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1(C)C=CC=CC=1>[CH2:16]([NH:23][C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[CH:8]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 995955,8-Dimethoxy-2-tetralone

Product 1

HCID 99946622-Benzylamino-5,8-dimethoxy-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

A mixture containing 82 mmol of 5,8-dimethoxy-3,4-dihydronaphthalen-2(1H)-one, 82 mmol of benzylamine and 0.20 g of p-toluenesulfonic acid is brought to reflux with azeotropic distillation of the water/toluene mixture. After heating for 2 hours, the mixture is cooled, filtered and the solvent evaporated under vacuum and leads to the expected product in the form of an oil.

Workup

  1. temperatureAfter heating for 2 hours
  2. temperaturethe mixture is cooled
  3. filtrationfiltered
  4. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-ce4f4af2d02648e4ab62477824c8d3f9
Source dataset
uspto-grants-1995_11
Patent number
US05464859

Reaction notes

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