Triethylamine → HCID 178502672, Verbindung

HRID 1690175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690175
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][O:12]CN.C1(N=C=[N:23][CH:24]2CCCCC2)CCCCC1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:11][O:12][N:23]([CH3:24])[C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[OH:1]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 177781771-MethoxymethanamineHCID 178418543HCID 178418543, Verbindung

Produkt 1

HCID 178502672HCID 178502672, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Hydroxynicotinic acid (2.00 g, 14.4 mmol) and methoxymethylamine (2.80 g, 28.8 mmol) were dissolved in methylene chloride (70 mL). The resultant mixture was added with dicyclohexylcarbodiimide (5.90 g, 28.8 mmol), triethylamine (4.00 mL), and 4-N,N-dimethylaminopyridine (176 mg, 1.44 mmol) at 0° C. The resultant mixture was stirred at room temperature overnight. Then the reaction solution was added with a small amount of water and concentrated in vacuo. Ethyl acetate was added and the generated crystal was filtered. Ethyl acetate was further added and the generated crystal was filtered in the same manner. The obtained residue was purified using silica-gel column chromatography (n-hexane/ethyl acetate=1/1) and N-methoxy-N-methyl-2-hydroxynicotinamide (2.18 g, yield 84%) was obtained as a colorless solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionEthyl acetate was added
  3. filtrationthe generated crystal was filtered
  4. additionEthyl acetate was further added
  5. filtrationthe generated crystal was filtered in the same manner
  6. customThe obtained residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-64a84ce9b0fa45dc8471a62f12d9138e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153634B2

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