Sodium Hydroxide → [4-(3-Phenyl-1,6-naphthyridin-2-yl)phenyl]methanol

HRID 604997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604997
C([Si](C)(C)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(C)(C)C.[NH2:25][C:26]1[C:31]([CH:32]=O)=[CH:30][N:29]=[CH:28][CH:27]=1.[OH-].[Na+]>C(O)C>[C:16]1([C:15]2[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH2:7][OH:6])=[CH:13][CH:12]=3)=[N:25][C:26]3[C:31]([CH:32]=2)=[CH:30][N:29]=[CH:28][CH:27]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 27610334-AminonicotinaldehydeHCID 598461331-[4-({[t-Butyl-(dimethyl)silyl]oxy}methyl)phenyl]-2-phenylethanone

Produkt 1

HCID 59846143[4-(3-Phenyl-1,6-naphthyridin-2-yl)phenyl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a partial suspension of 1-[4-({[t-butyl-(dimethyl)silyl]oxy}methyl)phenyl]-2-phenylethanone (1.36 gm, 4.0 mmol) and 4-aminonicotinaldehyde (prepared as described in J. Org. Chem. 48, 3401 (1983)) (540 mg, 4.42 mmol) in absolute ethanol (10 mL) was added dropwise 5N NaOH (3 mL, 15 mmol). This mixture was heated at 70° C. for three hours. The solvent was evaporated in vacuo and the residue was partitioned between methylene chloride and aqueous sodium carbonate. The organic layer was dried (Na2SO4), the solution filtered, and the solvent evaporated. This residue was triturated with a small amount of ethyl acetate as the product crystallized out. The mother liquors were chromatographed on silica gel eluting with 0-2% methanol/ethyl acetate (sat'd with ammonia) to give additional product. 1H-NMR (500 MHz, CDCl3): δ 9.32 (1H, s), 8.77 (1H, d, J=5.9 Hz), 8.29 (1H, s), 7.99 (1H, d, J=6.1 Hz), 7.46 (2H, d, J=8 Hz), 7.28-7.33 (5H, m), 7.24-7.26 (2H, m), 4.71 (2H, s),

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between methylene chloride and aqueous sodium carbonate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationthe solution filtered
  5. customthe solvent evaporated
  6. customThis residue was triturated with a small amount of ethyl acetate as the product
  7. customcrystallized out
  8. customThe mother liquors were chromatographed on silica gel eluting with 0-2% methanol/ethyl acetate (sat'd with ammonia)
  9. customto give additional product

Quellen und Nachweise

ORD-Eintrag
ord-8a2a8caee9be41e6bdafd719a562c147
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910561B2

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