6-Aminomethylquinoline Chemical Properties

Boiling point:

159°C/2mmHg(lit.)

Density 

1.156±0.06 g/cm3(Predicted)

refractive index 

1.6410-1.6450

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

Solid

pka

8.68±0.30(Predicted)

color 

Colorless to Yellow to Orange

Safety Information

HazardClass 

IRRITANT

HS Code 

2933499090

6-Aminomethylquinoline Usage And Synthesis

Uses

6-Quinolinemethanamine is a reagent in the synthesis of some novel 7-[(quinolin-6-yl)methyl] purines as potential c-Met inhibitors.

Synthesis

Step 5: Synthesis of quinolin-6-ylmethylamine To a saturated ammonia methanol solution (1 L) of quinoline-6-carbonitrile (96 g, 0.62 mol) was added Raney-Ni catalyst (10 g) and the reaction mixture was stirred at room temperature. The reaction was carried out for 16 hours at room temperature and 1 atmosphere of hydrogen at 1 atm. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 6-aminomethylquinoline as a brown oil (80 g, 82% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.83 (dd, J = 4.2, 1.7 Hz, 1H), 8.29 (d, J = 8.3 Hz, 1H), 7.95 (d, J = 8.6 Hz, 1H), 7.85 (s, 1H), 7.75 (dd, J = 8.7, 1.8 Hz, 1H), 7.49 (dd, J = 8.2, 4.2 Hz, 1H), 3.90 (s, 2H).

References

[1] ChemSusChem, 2017, vol. 10, # 5, p. 842 - 846
[2] Patent: US2011/281865, 2011, A1. Location in patent: Page/Page column 83
[3] Patent: WO2011/145035, 2011, A1. Location in patent: Page/Page column 108
[4] Patent: WO2013/144737, 2013, A2. Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1. Location in patent: Paragraph 0508

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