Triethylamine → 3-Benzyloxy-6-methylpyridine-2-carbonitrile

HRID 228748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228748
[CH2:1]([O:8][C:9]1[C:10]([CH:16]=O)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO.C([N:23](CC)CC)C.[N+](C1C=C2C(=O)OC(=O)C2=CC=1)([O-])=O>C(#N)C.O>[CH2:1]([O:8][C:9]1[C:10]([C:16]#[N:23])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2309764-Nitrophthalic acid anhydrideHCID 443297Hydroxyamine hydrochlorideHCID 227117753-(Benzyloxy)-6-methylpicolinaldehyde

Produkt 1

HCID 230785123-Benzyloxy-6-methylpyridine-2-carbonitrileAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Benzyloxy-6-methyl-pyridine-2-carbaldehyde (100 mg) was dissolved in acetonitrile (5 ml) to prepare a solution. Hydroxylamine hydrochloride (72 mg) and triethylamine (0.25 ml) were added to the solution, and the mixture was stirred at room temperature for one hr. 4-Nitrophthalic anhydride was added to the reaction solution, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using ethyl acetate-hexane to give 3-benzyloxy-6-methylpyridine-2-carbonitrile (53 mg, yield 54%).

Aufarbeitung

  1. customto prepare a solution
  2. stirringthe mixture was stirred at 100° C. overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bdfee52e07bc4b12b80fbb8208671e1d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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