1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL HBR Chemical Properties

Melting point:

196.7-197.8℃

storage temp. 

Inert atmosphere,Room Temperature

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933491090

1,2,3,4-TETRAHYDRO-ISOQUINOLIN-6-OL HBR Usage And Synthesis

Uses

1,2,3,4-Tetrahydro-6-isoquinolin-6-ol Hydrobromide is a chemical reagent used in the organic synthesis. Used in the preparation of androgen receptor modulators (SARMs) as well as steroidmimetic and chimeric microtubule disruptors.

Synthesis

General procedure for the synthesis of 1,2,3,4-tetrahydroisoquinolin-6-ol hydrobromide from 6-methoxy-1,2,3,4-tetrahydroisoquinoline: 6-methoxy-1,2,3,4-tetrahydroisoquinoline (2.12 g, 13.0 mmol) was dissolved in 48% aqueous hydrobromic acid. The reaction mixture was stirred at 120°C for 3 hours. After completion of the reaction, the solvent was removed by vacuum concentration. The obtained residue was suspended in ethyl acetate and the solvent was evaporated again to afford 1,2,3,4-tetrahydroisoquinolin-6-ol hydrobromide (2.99 g, 95% yield) as a reddish brown solid. The product was characterized by 1H NMR (300 MHz, D2O): δ 7.10 (d, J = 8.4 Hz, 1H), 6.82-6.75 (m, 2H), 4.28 (s, 2H), 3.48 (t, J = 6.3 Hz, 2H), 3.05 (t, J = 6.3 Hz, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 789 - 801
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 12, p. 2208 - 2216
[3] Patent: US6562828, 2003, B1
[4] Patent: US5936089, 1999, A
[5] Patent: WO2007/146122, 2007, A2. Location in patent: Page/Page column 42

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