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Acetic Acid → 4-(6-Methyl-5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

HRID 604999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 604999
[O:1]=[C:2]1[NH:11][CH:10]=[CH:9][C:8]2[N:7]=[C:6]([C:12]3[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=3)[C:5]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:4][C:3]1=2.[H-].[Na+].CI.[C:30](O)(=O)C>CN(C=O)C.C(OCC)(=O)C>[CH3:30][N:11]1[CH:10]=[CH:9][C:8]2[N:7]=[C:6]([C:12]3[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=3)[C:5]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:4][C:3]=2[C:2]1=[O:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

Produkt 1

HCID 866249424-(6-Methyl-5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (186 mg, 0.57 mmol) in dry DMF (2 mL) was added 60% sodium hydride in mineral oil (29 mg, 0.72 mmol). The reaction was stirred at room temperature for 15 minutes and then methyl iodide was added via syringe (40 μL, 0.70 mmol). After 30 minutes the reaction was diluted with ethyl acetate and some acetic acid was added to neutralize the base. The solution was washed with aqueous NaHCO3 and the organic layer was dried (anhydrous Na2SO4), filtered and the solvent evaporated. The residue was triturated with diethyl ether to give the title compound as a pale yellow solid. The mother liquors were chromatographed on silica gel eluting with a 30-70% ethyl acetate/hexane gradient to give additional product. 1H-NMR (500 MHz, CDCl3): δ 10.02 (1H, s), 8.74 (1H, s), 7.80 (2H, d, J=8 Hz), 7.60 (2H, d, J=8 Hz), 7.37 (1H, d, J=7.6 Hz), 7.28-7.31 (2H, m), 7.19-7.22 (2H, m), 6.85 (1H, d, J=7.6 Hz), 3.67 (3H, s). m/e (m+1): 341.1.

Aufarbeitung

  1. washThe solution was washed with aqueous NaHCO3
  2. dry with materialthe organic layer was dried (anhydrous Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-789aed7ff6454838acf2c675b0cbb8a4
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910561B2

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