Diisopropylethylamine → 4-chloro-N-isobutoxypicolinamide

HRID 1988484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988484
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](Cl)=[O:10])[CH:4]=1.Cl.[CH2:13]([O:17][NH2:18])[CH:14]([CH3:16])[CH3:15].C(N(CC)C(C)C)(C)C>C1COCC1.O.CCOC(C)=O>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:18][O:17][CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH:4]=1

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 12696238O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1)HCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

Produkt 1

HCID 577256094-chloro-N-isobutoxypicolinamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloropicolinoyl chloride hydrochloride (1.0 g, 5.68 mmol, 1.0 eq) in 25 ml of THF were added O-isobutylhydroxylamin hydrochloride (785 mg, 6.25 mmol, 1.1 eq) and N,N-diisopropylethylamine (2.97 ml, 17.0 mmol, 3.0 eq) at room temperature. The reaction mixture was stirred for 30 min and diluted with water (25 mL) and EtOAc (50 mL). The separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (2×25 mL) and dried over sodium sulfate. Concentration under reduced pressure gave the title compound as colorless solid (870 mg, 67%), which was used without further purification. ES/MS m/z 229.0 (MH+), Rt=2.61 min.

Aufarbeitung

  1. washThe separated organic layer was washed with brine (25 mL), saturated sodium bicarbonate solution (2×25 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-15723ee71d374e4099b32fe97f5e780a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553854B2

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