Sodium hydride → 8-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4](F)[CH:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(4-chloro-2-fluorophenyl)-N,2-dimethylnicotinamide (40 mg, 0.144 mmol) in THF (3 mL) cooled to 0° C. was added NaH (10.33 mg, 0.431 mmol) and the reaction mixture was stirred for 4 h. After the reaction completion, the reaction mixture was quenched with ice water and the product was extracted with ethyl acetate (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (30 mg, 0.116 mmol, 81% yield) as an off-white solid. LC/MS, (ESI) m/z 259.2 [(M+H)+, calcd for C14H12ClN2O 259.1]; LC/MS retention time (Method D): tR=0.65 min.