1,2-Dichloroethane → Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1406683

Reaktionsgleichung

Reaktionsgleichung von HRID 1406683
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10](O)(=[O:14])[CH:11]([CH3:13])[CH3:12].C1C=C2N=NN(O)C2=CC=1.O.C(Cl)CCl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[N:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 6590Isobutyric AcidHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199167865-Fluoro-2-hydrazinylpyridine

Produkt 1

HCID 66977821Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-fluoro-2-hydrazinyl-pyridine (0.59 g, 4.65 mmol), isobutyric acid (528 mg, 6 mmol), and HOBt hydrate (153 mg, 1 mmol) in DCM (10 mL) was treated with EDC (1.15 g, 6 mmol). The reaction mixture was stirred at RT for 40 min, poured onto sat. aq. sodium bicarbonate (40 mL), extracted with four portions of DCM, dried (Na2SO4), evaporated and purified by FCC using 10-30% EtOAc/DCM to give the title compound (0.42 g, 46%). LCMS (method 2): Rt 2.46 min, m/z 198 [MH+].

Aufarbeitung

  1. extractionextracted with four portions of DCM
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. custompurified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-f64fbdcf1c55469ca59147b1d94fad71
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916708B2

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