6-Isoquinolinol

white to light yellow crystal powder

(c) b) ISOQUINOLIN-6-OL Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3percent of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27percent) : 8H (DMSO-d6, 400 MHz): 7.09 (s, 1H), 7.19 (dd, 1H, J=9, 2 Hz), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H).Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160°C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3percent of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27percent) : No.H (DMSO-d6, 400 MHz) : 7.09 (s, 1H), 7.19 (dd, 1H, J = 9, 2H2), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H)AB21-1 (lg, 4.83 mmol) was dissolved in dioxane (5 mL) Adding tris (dibenzylideneacetone) dipalladium (lllmg, 0.19 mmol) and 2-di-tert-butylphosphine 2 ', 4', 6'-triisopropylbiphenyl (82 mg, 0.19 mmol) Then, potassium hydroxide (812 mg, 14.49 mmol) dissolved in 5 mL of water was added and heated to 100 ° C for 1.5 hours. After cooling to room temperature, 2N HCl (20 mL) was added, stirred for 1 hour, concentrated under reduced pressure, extracted with dichloromethane (30 mL * 3). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a pale yellow solid (526 mg, 75percent).(c) 6-Methoxyisoquinoline (16 g, 0.1M) and 48% aqueous HBr (600 ml) were refluxed together for 6 hours and the mixture was then evaporated to dryness in vacuo. The residue was dissolved in H2 O and basified with solid Na2 CO3. The resulting precipitated solid was filtered off and recrystallized from isopropanol to give Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3% of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27%) : No.H (DMSO-d6, 400 MHz) : 7.09 (s, 1H), 7.19 (dd, 1H, J = 9, 2H2), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H)b) ISOQUINOLIN-6-OL Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3% of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27%) : 8H (DMSO-d6, 400 MHz): 7.09 (s, 1H), 7.19 (dd, 1H, J=9, 2 Hz), 7.56 (d, 1H, J = 6 Hz), 7.94 (d, 1H, J = 9 HZ), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H).Isoquinolin-6-ol Heat a mixture of 6-methoxy-isoquinoline (2.1 g, 13.2 mmol) and pyridine hydrochloride (30 g) in a heavy walled screw cap sealed tube at 160C overnight. Cool to room temperature, add water and concentrated ammonium hydroxide to bring the pH of the mixture to 10-11, extract with ethyl acetate (4 times), wash the combined organic extracts with water (4 times), and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-3% of 2N NH3/MeOH in dichloromethane afford the title compound (520 mg, 27%): 8H (DMSO-d6, 400 MHz) : 7.09 (s, 1H), 7.19 (dd, 1H, J = 9, 2 HZ), 7.56 (d, 1H, J = 6 HZ), 7.94 (d, 1H, J = 9 Hz), 8.29 (d, 1H, J = 6 Hz), 9.05 (s, 1H), 10.36 (s, 1H).General procedure: For screening the benzylisoquinoline alkaloids O-glycosylation activity of CtGTs, the small molecules, 5-Hydroxyisoquinoline (1), General procedure: The hydrolysis reaction was as follows: The mixture ofbromoisoquinoline (11.2 g, 50.5 mmol), hydrated CuSO4 (5 g, 20.l mmol), copper bronze (4.1 g, 64.1 mmol), and NaOH (31.3g, 757.5 mmol) in water (17 mL) was heated in an autoclaveat 210°C for 12 h. After cooling to room temperature, themixure was filtered and the solid cake was washed with water, the combined filtrate was adjusted to pH 6 with hydrochloricacid to precipitate the solid (i4-i8)2Cu.5H2O. The Na2S.9H2O (5 g, 24.5 mmol) was add to a solutionof (i4-i8)2Cu.5H2O (21.75 g 49 mmol) in 200 mL EtOH, andstirred at 40°C for 20 h and then filtered. Removal of excess ofsolvent afforded solid, the solid to water (500 mL), and adjustedto pH 6 with hydrochloric acid to give i4-i8 as off-white solid.[CAS Reg. No. 1822782-90-0] DIAD (1.22 mL, 6.20 mmol) was added to a mixture of

Molecular Weight:145.16
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:145.052763847
Monoisotopic Mass:145.052763847
Topological Polar Surface Area:33.1
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes