Triethylamine → 2-(Pyridin-2-ylmethoxy)-isoindole-1.3-dione

HRID 39305

Reaktionsgleichung

Reaktionsgleichung von HRID 39305
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:10][N:11]1[C:12](=[O:21])[C:13]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]2[C:15]1=[O:16]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 23392Picolyl chloride hydrochloride

Produkt 1

HCID 122139452-(Pyridin-2-ylmethoxy)-isoindole-1.3-dioneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Chloromethylpyridine hydrochloride (514 mg, 3.13 mmol), N-hydroxyphthalimide (515 mg, 3.18 mmol), and triethylamine (1.3 mL, 9.3 mmol) were mixed in acetonitrile (5 mL) and stirred at 80° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with 1N NaOH(aq), water, and brine. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was recrystallized from ethyl acetate and hexanes to provide N-(pyridine-2-ylmethoxy)phthalimide (364 mg, 1.44 mmol).

Aufarbeitung

  1. washwashed sequentially with 1N NaOH(aq), water, and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a0c6c07c91f64f5fb80b8604da9ff8f9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524764B2

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