1-Methyl-3,4-dihydro-1H-naphthalen-2-one → 10b-Methyl-3,5,6,10b-tetrahydro-benzo[f]quinoline

HRID 520991Notes

Reaction equation

[CH2:1]([NH2:4])[C:2]#[CH:3].[CH3:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=O>C(O)C>[CH3:5][C:6]12[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]1=[N:4][CH2:1][CH:2]=[CH:3]2

Participants

Conditions

Temperature: 100 °C

Procedure

Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+.

Workup

additioncharged with a stir bar
custommay evolve afterwards→keep an ice bath at hand
temperatureAfter cooling the mixture to room temperature
customthe solvent is evaporated
customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)

Sources & evidence

ORD record: ord-d181a80036974640b2ff74a1c873a25f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328072B2

Reaction notes

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