Hydrochloric Acid → 4-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

HRID 605010Notes

Reaction equation

HRID 605010 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[O:28]C)[N:13]=2)=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[O:28]=[C:18]1[NH:17][CH:16]=[CH:15][C:14]2[N:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=3)[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 592646202-[4-(1,3-Dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine

Product 1

HCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-[4-(1,3-dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine (25 g, 66 mmol) in dioxane (66 mL) was added 4M HCl (66 mL). The reaction mixture was stirred overnight, poured carefully into saturated NaHCO3 (900 mL), and filtered to give 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde as a white solid. 1H NMR: (500 MHz, CDCl3) δ 11.58 (br s, 1H), 10.00 (s, 1H), 8.74 (s, 1H), 7.80 (d, 2H), 7.61 (d, 2H), 7.43 (d, 1H), 7.33-7.21 (m, 6H), 6.93 (d, 1H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-d69715c841f84a808591e4afae7ff88e
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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