1,4-Dioxane hydrochloride → 6-bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-one
Reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Br:18])=[CH:15][N:16]=2)[C:11](=[O:19])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[Br:18][C:14]1[CH:13]=[C:12]2[C:17](=[N:16][CH:15]=1)[NH:8][CH2:9][CH2:10][C:11]2=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (628 mg, 1.92 mmol) is dissolved into 3 mL of MeOH and 3 mL of 4 M HCl/1,4-dioxane is added. The mixture is stirred for 16 h and concentrated to dryness. The residue is dissolved into 10 mL CH2Cl2 and 10 mL of H2O and neutralized with saturated aqueous Na2CO3 solution. The aqueous layer is extracted with 2×20 mL of CH2Cl2. The organic phase is dried with MgSO4, filtered and concentrated to give 386 mg of 6-bromo-2,3-dihydro-1H-[1,8]naphthyridin-4-one