Methyl 4-hydrazinylbenzoate → Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate

HRID 509719

Reaktionsgleichung

Reaktionsgleichung von HRID 509719
[NH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[NH2:2].Br[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[N:20][CH:21]=1>C(N(CC)CC)C>[CH3:22][C:19]1[N:20]=[CH:21][C:16]([CH2:15][CH2:14][N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)[NH2:2])=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 408928Methyl 4-hydrazinylbenzoateHCID 533058565-(2-Bromoethyl)-2-methylpyridine

Produkt 1

HCID 68735268Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoateAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Methyl 4-hydrazinylbenzoate (1 g, 0.005 moles) and 5-(2-bromoethyl)-2-methylpyridine (1 g, 0.005 moles) was taken up in triethylamine (2.1 mL) and stirred at RT for 1 hr. The reaction was heated at 100° C., overnight. LCMS analysis of the reaction mixtures shows the formation of product. The reaction mixture was concentrated, water (20 mL) was added to the reaction mixture and the mixture extracted with ethyl acetate. The crude product was dissolved in ethyl acetate and purified by column chromatography using neutral alumina, using 100% ethyl acetate as the eluent. After chromatography 400 mg of Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate was obtained, 28.5% yield.

Aufarbeitung

  1. temperatureThe reaction was heated at 100° C., overnight
  2. customLCMS analysis of the reaction mixtures
  3. concentrationThe reaction mixture was concentrated
  4. additionwater (20 mL) was added to the reaction mixture
  5. extractionthe mixture extracted with ethyl acetate
  6. dissolutionThe crude product was dissolved in ethyl acetate
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c6ac98b775524cb3a8456186163c2323
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096591B2

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