Sodium borohydride → HCID 67324605, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH:17]=[O:18])[CH:6]=[CH:5]2.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:15]#[N:16])[C:11]=1[N:12]([CH3:14])[CH3:13])[N:8]=[C:7]([CH2:17][OH:18])[CH:6]=[CH:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The 6-bromo-7-dimethylamino-2-formylquinolin-8-carbonitrile (2.4 g, 7.9 mmol, 1.0 eq) was added to MeOH (20 mL) at 0° C. Sodium borohydride (328 mg, 8.7 mmol, 1.1 eq) was then introduced and the mixture was stirred at room temperature for 1 hour. The solution was quenched with HCl 1 M, ethanol was evaporated and water was added. The solution was extracted with dichloromethane and the organic layer was washed twice with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The 6-bromo-7-dimethylamino-2-(hydroxymethyl)quinoline-8-carbonitrile was obtained as an orange solid (2.4 g, 98%).