Hydrogen Peroxide → 3-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

HRID 1626128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626128
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH:11]O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:11])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1

Komponenten

4

Edukt 2

HCID 784Hydrogen PeroxideHCID 681078143-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Produkt 1

HCID 580828393-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine (3.03 g, 19.7 mmol) in acetic acid (19.7 ml) was treated at room temperature with hydrogen peroxide (3.45 ml, 39.5 mmol). The mixture was heated to 70° C. and stirred at this temperature overnight. After completion, the reaction mixture was allowed to cool and was concentrated at reduced pressure. Water was added and the mixture was evaporated again. This procedure was repeated another 2 times. The residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, then dried over sodium sulfate and evaporated at reduced pressure. The crude 3-chloro-6,7-dihydro-5H-[1]pyrindine 1-oxide was obtained as dark green crystals (2.07 g, 62% yield). MS (ISP): m/z=170 [M+H]+.

Aufarbeitung

  1. temperatureto cool
  2. concentrationwas concentrated at reduced pressure
  3. additionWater was added
  4. customthe mixture was evaporated again
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4561bdeb29454057a1d134c42821bee4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785436B2

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