ChemicalBook CAS DataBase List 1,2,3,4-Tetrahydro-8-hydroxyquinoline

1,2,3,4-Tetrahydro-8-hydroxyquinoline synthesis

8synthesis methods

Product Name:1,2,3,4-Tetrahydro-8-hydroxyquinoline
CAS Number:6640-50-2
Molecular formula:C9H11NO
Molecular Weight:149.19

130-16-5 Synthesis

130-16-5
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$5.00/5g

6640-50-2
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$9.00/250mg

Yield: 72%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in tetrahydrofuran;methanol at 20; under 760.051 Torr; for 24.5 h;Solvent;

Steps:

1,2,3,4-Tetrahydro-8-quinolinol (Compound 3)
Compound 1a (5-chloro-8-quinolinol: 1.26 g, 7.00 mmol)was dissolved in 14 mL of a mixture containing THF andMeOH (1 : 1), added to 10% Pd/C (744.9 mg, 0.70 mmol), andhydrogenated at 1 atm in H2 gas at room temperature. Afterbeing stirred for 24.5 h, the reaction mixture was filtered,and the filtrate was concentrated under reduced pressure. Thecrude product was purified by recrystallization with CHCl3 toafford compound 3 (724.0 mg, 72%) as a pale orange crystal.Analytical data on compound 3 was as follows: 1H-NMR(CD3OD, 400 MHz) δ: 2.05-2.15 (m, 2H), 2.89 (t, J = 6.1 Hz,2H), 3.41-3.49 (m, 2H), 6.78 (d, J = 7.5 Hz, 1H), 6.82 (d,J = 8.1 Hz, 1H), 7.20 (dd, J = 8.1, 7.5 Hz, 1H); 13C-NMR(CDCl3 + MeOH-d4 5 drop, 100 MHz) δ: 19.5, 24.9, 42.5,113.8, 118.1, 120.5, 129.3, 132.2, 150.7; HR-MS (EI) Calcd forC9H11NO ([M]+): 149.0841. Found: 149.0836.

References:

Karuo, Yukiko;Kawai, Kentaro;Nakahara-Yamada, Mayuko;Nishimura, Hitoshi;Omote, Masaaki;Sato, Kazuyuki;Shiraki, Riona;Tarui, Atsushi;Tsunokawa, Ryo;Yoshida, Ayaka [Chemical and Pharmaceutical Bulletin,2021,vol. 69,# 6,p. 557 - 563]

148-24-3 Synthesis