Sodium borohydride → (1-Chloroisoquinolin-5-yl)methanol
Reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-chloro-5-isoquinolinecarboxaldehyde (308 mg, 1.6 mmol) and sodium borohydride (NaBH4) (68 mg, 1.8 mmol) in MeOH (6 mL) was stirred at room temperature for 2 h. The reaction was quenched with water (2 mL) and concentrated in vacuo. The residue was suspended in CH2Cl2, washed with water, with brine and then dried over MgSO4 and evaporated. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (80:20 to 50:50) as eluant to give 1-chloro-5-(hydroxymethyl)isoquinoline (240 mg, 1.23 mmol) as a white solid.