p-Toluenesulfonic acid → 8-Bromo2-dipropylamino-3,4-dihydronaphthalene

HRID 256563Notes

Reaction equation

HRID 256563 reaction equation
[Br: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.[CH2:13]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([N:16]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8902DipropylamineHCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 190432078-Bromo2-dipropylamino-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8-bromo-2-tetralone (3.0 gm, 13.3 mMol) in toluene (25 mL) were added di-n-propylamine (3.5 mL, 26 mMol) and p-toluenesulfonic acid (100 mg, 0.52 mMol). The reaction was heated to reflux, water being collected in a Dean-Stark trap. After four hours the reaction was concentrated in vacuo to give 8-bromo-2-dipropylamino-3,4-dihydronaphthalene as a dark liquid which was immediately dissolved in methanol (50 mL) and acetic acid (5 mL). To this solution was then added sodium borohydride (2.0 gm, 52.9 mMol), and the mixture was stirred 18 hours at room temperature.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customwater being collected in a Dean-Stark trap
  4. concentrationAfter four hours the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c4c4d1d7dee4450397d8dd5c3042dd8b
Source dataset
uspto-grants-1993_11
Patent number
US05258379

Reaction notes

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