Sodium methanethiolate → 6-Isoquinolinol, 7-methyl- (9CI)

HRID 228875Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[CH:9]=[N:8][CH:7]=[CH:6]2.C[S-].[Na+]>CN(C)C=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

Conditions

Temperature: 160 °C

Procedure

6-Methoxy-7-methylisoquinoline (239 mg) and sodium thiomethoxide (1.58 g) were suspended in N,N-dimethylformamide (12 ml), and the suspension 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 6-hydroxy-7-methylisoquinoline (21 mg, yield 1%).

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-59963b43ab36432bae428be123756b9a
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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