Morpholine → 4-Morpholino-2-nitrobenzonitrile

HRID 1431245

Reaktionsgleichung

Reaktionsgleichung von HRID 1431245
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1COCC1>[O:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:14][CH2:15]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 969244-Chloro-2-nitrobenzonitrile

Produkt 1

HCID 134992654-Morpholino-2-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-chloro-2-nitrobenzonitrile (2.0 g, 11 mmol) in THF (40 mL) was added morpholine (1.0 g, 11 mmol). The reaction was heated at reflux overnight. After this time the reaction was cooled to rt and then it was partitioned between EtOAc (150 mL) and NaHCO3 (50 mL, satd aq. solution). The separated organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:1) gave 4-morpholino-2-nitrobenzonitrile.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customit was partitioned between EtOAc (150 mL) and NaHCO3 (50 mL, satd aq. solution)
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9b10deb16b3e47efb2cf95c1b8f87c24
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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