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

HRID 604987Notes

Reaction equation

HRID 604987 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][CH3:29])[N:13]=2)=[CH:8][CH:7]=1.Cl.C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:29][O:28][C:18]1[N:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH:20]=[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=1)=[N:13]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 592646202-[4-(1,3-Dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine

Product 1

HCID 598461374-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(1,3-dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine (760 mg, 1.98 mmol) in THF (8 mL) was added 1 N HCl (6 mL) and the solution was stirred for three hours. Ethyl acetate was added and the mixture was made basic with aqueous Na2CO3. The organic layer was dried (Na2SO4), filtered and the solvent evaporated. The residue was triturated with diethyl ether to give pure product. The mother liquors were purified by column chromatography on silica gel and elution with 10-30% ethyl acetate/hexane gave additional product. 1H-NMR (500 MHz, CDCl3): δ 10.10 (1H, s), 8.60 (1H, s), 8.26 (1H, d, J=6 Hz), 7.81 (2H, d, J=8.3 Hz), 7.62 (2H, d, J=8.3 Hz), 7.56 (1H, d, J=6.1 Hz), 7.30-7.32 (3H, m), 7.21-7.23 (2H, m), 4.17 (3H, s). m/e (m+1): 341.1.

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. filtrationfiltered
  3. customthe solvent evaporated
  4. customThe residue was triturated with diethyl ether
  5. customto give pure product
  6. customThe mother liquors were purified by column chromatography on silica gel and elution with 10-30% ethyl acetate/hexane
  7. customgave additional product

Sources & evidence

ORD record
ord-2209d1651f3e4e72a39c3b95aaa4406e
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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