2-Tetralone → 5,6-Dihydro-benzo[f]quinoline

HRID 2271981Notes

Reaction equation

HRID 2271981 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH2:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=O>C(O)C>[CH:3]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:14]=3[CH2:13][CH2:12][C:11]=2[N:4]=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 682662-TetraloneHCID 239041Propargylamine

Product 1

HCID 158731845,6-Dihydro-benzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Propargylamine (5 mL) is added to a flask charged with a stir bar, 2-tetralone (10.00 g), NaAuCl4*2H2O (0.65 g), and ethanol (50 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred at room temperature for 15 min and then at reflux temperature for 1 h. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40) to afford the title compound as an oil. Yield: 6.78 g (56% of theory); LC (method 1): tR=1.81 min; Mass spectrum (ESI+): m/z=182 [M+H]+. Alternatively, the reaction may be conducted in a microwave oven heating with microwave irradiation to 100° C. for 10 min.

Workup

  1. additioncharged with a stir bar
  2. custommay evolve afterwards→keep an ice bath at hand
  3. temperatureat reflux temperature for 1 h
  4. temperatureAfter cooling the mixture to room temperature
  5. customthe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40)

Sources & evidence

ORD record
ord-2038b71dfe734d9986784ead32bdf204
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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