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

HRID 645937Notes

Reaction equation

HRID 645937 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-5574197c0f274b07b47dcbe0cb0f2d6e
Source dataset
uspto-grants-2010_04
Patent number
US07705014B2

Reaction notes

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