O-Methylhydroxylamine hydrochloride → HCID 62553448, Verbindung

HRID 2233424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233424
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=O)=[CH:3][CH:2]=1.Cl.O([NH2:20])C>FC(F)(F)C(O)=O.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([NH2:20])[C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 113562871-(3-Methylphenyl)-2-(pyridin-4-yl)ethan-1-one

Produkt 1

HCID 62553448HCID 62553448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

The intermediate oxime was prepared from 2-pyridin-4-yl-1-m-tolyl-ethanone (crude) and methoxylamine hydrochloride (8.00 g, 95.78 mmol) according to the protocol described in general procedure B. The oxime was then dissolved in trifluoroacetic acid (30.00 mL) and Pd/C (0.80 g) was added. The reaction mixture was hydrogenated under 50 psi for 14 hours, then filtered and concentrated. The residue was basified with 5M sodium hydroxide and extracted with methylene chloride. The combined organic phases were dried over potassium carbonate and concentrated to yield the title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 3H) 2.89 (d, J=7.04 Hz, 2 H) 4.12 (t, 1 H) 7.10-7.22 (m, 1 H) 7.39 (ddd, J=7.77, 4.25, 1.47 Hz, 2 H) 7.75-7.82 (m, 1H) 8.41 (td, J=4.98, 2.05 Hz, 2 H) 8.58 (dd, J=5.86, 1.76 Hz, 2 H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic phases were dried over potassium carbonate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3d700f68197844d594d12233cbba9d89
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709507B2

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