1,2,3,4-TETRAHYDROQUINOLIN-6-OL Chemical Properties

Melting point:

160 °C

Boiling point:

337.5±31.0 °C(Predicted)

Density 

1.141±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Methanol

form 

Solid

pka

11.48±0.20(Predicted)

color 

Off-White

Safety Information

HS Code 

2933499090

1,2,3,4-TETRAHYDROQUINOLIN-6-OL Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

A potential amoebicide.

Synthesis

General procedure for the synthesis of 6-hydroxy-1,2,3,4-tetrahydroquinoline from 6-methoxy-1,2,3,4-tetrahydroquinoline: 6-methoxy-1,2,3,4-tetrahydroquinoline (3.00 g, 18.38 mmol) was dissolved in 50 mL of dichloromethane, and boron tribromide (13.81 g, 55.14 mmol) was slowly added at 0 °C. The reaction system was then warmed up to 15 °C with continuous stirring for 2 hours. After completion of the reaction, the reaction solution was concentrated and the reaction was quenched with 5 mL of methanol. To the reaction mixture, 20 mL of saturated sodium bicarbonate solution was added and stirred for 30 minutes. The reaction was extracted three times with 20 mL of ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate. The organic phase was concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent ratio: petroleum ether/ethyl acetate from 3:1 to 1:1 gradient elution) to finally obtain 6-hydroxy-1,2,3,4-tetrahydroquinoline (1.95 g, yield 71.11%). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.24 (s, 1H), 6.22-6.35 (m, 3H), 4.93 (br.s, 1H), 3.02-3.10 (m, 2H), 2.57 (t, J = 6.4 Hz, 2H), 1.67-1.80 (m, 2H).

References

[1] Patent: EP3293177, 2018, A1. Location in patent: Paragraph 0222; 0224
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418

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