Pyridine → 1H-Indole-6-carbaldehyde O-methyl-oxime

HRID 2236430

Reaktionsgleichung

Reaktionsgleichung von HRID 2236430
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=O)[CH:8]=2)[CH:3]=[CH:2]1.N1C=CC=CC=1.Cl.[O:19]([NH2:21])[CH3:20]>O>[CH3:20][O:19][N:21]=[CH:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27734351H-Indole-6-carboxaldehyde

Produkt 1

HCID 722508601H-Indole-6-carbaldehyde O-methyl-oximeAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

An amount of 1H-Indole-6-carbaldehyde (50 mg, 0.34 mmol) is added to pyridine (2.0 ml) at room temperature, followed by addition of methoxylamine hydrogen chloride (31.6 mg, 0.38 mmol). The mixture is stirred at ambient temperature for 24 h, and 10 mL of water is added. After the solvents were evaporated, the residue is dissolved 10 mL of anhydrous ether, washed successively with 10 mL of aqueous sodium bicarbonate, 10 mL of sodium bisulfite, and 10 mL of brine. Dried over magnesium sulfate, evaporated to give a white solid (49 mg, 0.281 mmol). MS (ESI) m/z 176.3 (M+1)

Aufarbeitung

  1. customAfter the solvents were evaporated
  2. dissolutionthe residue is dissolved 10 mL of anhydrous ether
  3. washwashed successively with 10 mL of aqueous sodium bicarbonate, 10 mL of sodium bisulfite, and 10 mL of brine
  4. dry with materialDried over magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9755bd7b0d8e47f39496ab019f24d438
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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