2,6-Lutidine → 2-Hydroxyimino-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-N-(6-trifluoromethyl-pyridin-3-yl)-acetamide

HRID 1094379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094379
O=[C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([N:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)[C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)=[O:4].Cl.[NH2:35][OH:36].N1C(C)=CC=CC=1C>CCO>[OH:36][N:35]=[C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([N:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=1)[C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 443297Hydroxyamine hydrochlorideHCID 580075482-oxo-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-N-(6-trifluoromethyl-pyridin-3-yl)-acetamide

Produkt 1

HCID 866371132-Hydroxyimino-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-N-(6-trifluoromethyl-pyridin-3-yl)-acetamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-oxo-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-N-(6-trifluoromethyl-pyridin-3-yl)-acetamide (46 mg, 0.1 mmol) in EtOH (2 mL) was added hydroxylamine hydrochloride (14 mg, 0.2 mmol) and 2,6-lutidine (32 mg, 0.3 mmol) and the mixture stirred at ambient temperature for 36 h then concentrated and redissolved in EtOAc (5 mL), washed with 10% aqueous citric acid (3×5 mL), dried over Na2SO4, filtered, then purified by chromatography (SiO2, heptane:ethyl acetate=95:5 to 50:50) to afford the title compound (22 mg, 46%) as a white solid. MS m/e: 480.3 [M+H]+.

Aufarbeitung

  1. concentrationthen concentrated
  2. dissolutionredissolved in EtOAc (5 mL)
  3. washwashed with 10% aqueous citric acid (3×5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. custompurified by chromatography (SiO2, heptane:ethyl acetate=95:5 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-171b4f313b774ea4850f68fe67d630ac
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133909B2

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