Sodium Hydroxide → 3-((4-Methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinolin-8-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[C:18](=[O:19])[C:17]3[C:12](=[C:13]([C:20]#[N:21])[CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:22])[CH:10]=2)=[CH:5][CH:4]=1.[OH-:25].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:18](=[O:19])[C:17]3[C:12](=[C:13]([C:20]([NH2:21])=[O:25])[CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:22])[CH:10]=2)=[CH:23][CH:24]=1Participants
4
Procedure
A solution of 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-8-carbonitrile (1.75 g, 5.46 mmol) and 25% aqueous sodium hydroxide (20 mL) in methanol (100 mL) was stirred at reflux for 3 h. After complete consumption of the nitrile, the mixture was concentrated to remove ˜75% of the methanol. The mixture was acidified to pH 3 with 1 M HCl (aq), and partitioned between EtOAc and brine. The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. The crude product was absorbed onto silica gel and purified by automatic silica gel column chromatography (Combiflash RF), eluting with methanol/dichloromethane (0-30%) to afford 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-8-carboxamide (1.21 g, 3.58 mmol, 65.5% yield) as light brown solid. LCMS (M+H)+: 339.3.