Sodium methanethiolate → 7-Pyridin-2-yl-isoquinolin-6-ol

HRID 228883Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

6-Methoxy-7-pyridin-2-yl-isoquinoline (118 mg) and sodium thiomethoxide (350 mg) were suspended in N,N-dimethylformamide (3 ml), and the mixture was stirred at 150° C. for 4 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-2-yl-isoquinolin-6-ol (30 mg, yield 27%).

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-8075445007724bd081b256dfd0c1cf0e
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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