Sodium methanethiolate → 7-Pyridin-3-yl-isoquinolin-6-ol

HRID 228886Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:9]=[N:8][CH:7]=[CH:6]2.C[S-].[Na+]>CN(C)C=O>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][N:8]=[CH:9]3)=[CH:4][C:3]=2[OH:2])[CH:14]=1

Participants

Conditions

Temperature: 160 °C

Procedure

6-Methoxy-7-pyridin-3-yl-isoquinoline (42 mg) and sodium thiomethoxide (126 mg) were suspended in N,N-dimethylformamide (1.5 ml), and the mixture was stirred at 160° C. for 2 hr. The reaction solution was cooled to room temperature, the reaction solution was then filtered, and the solvent was removed from the filtrate by distillation under the reduced pressure. The residue was purified by thin layer chromatography using chloroform-methanol to give 7-pyridin-3-yl-isoquinolin-6-ol (7 mg, yield 17%).

Workup

temperatureThe reaction solution was cooled to room temperature
filtrationthe reaction solution was then filtered
customthe solvent was removed from the filtrate by distillation under the reduced pressure
customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record: ord-4fb894e1ec6a42caa0889f8dcf166f02
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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