tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate → 2-Oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile
Reaction equation
[C:1]([C:3]1[C:4](=[O:26])[N:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]2[CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][C:11]=2[CH:12]=1)#[N:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:26]=[C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[N:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-Butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (150 mg, 0.427 mmol) was dissolved in CH2Cl2 (3 mL) and TFA (0.3 mL). The mixture was stirred at room temperature overnight. All solvents were removed under vacuum to give crude 2-oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile. LCMS: m/z 252.15 (M+H)+, 0.78 min (method 7).