N,N-Dimethylaniline → 4-Cyclopropylpyridin-2-amine

HRID 1446703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446703
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C[N:11](C)C1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 2

HCID 949N,N-DimethylanilineHCID 36142304-Cyclopropylpyridine

Produkt 1

HCID 457879154-Cyclopropylpyridin-2-amineAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Reflux 4-cyclopropyl-pyridine (600 mg, 5 mmol), N,N-dimethylaniline (1.4 mL, 11 mmol) and NaNH2 (50% in toluene, 468 mg, 6 mmol) at 150-160° C. under nitrogen in toluene for overnight. Cool the mixture and dilute with water and ethyl acetate. Extract the organic layer by minimal amount of water. Dry the organic layer (combination of anhydrous MgSO4, Na2SO4 and K2CO3), concentrate and purify by silica gel column chromatography to obtain the title compound in 12% yield. LCMS (ES), m/z 135 (M+1).

Aufarbeitung

  1. temperatureCool the mixture
  2. extractionExtract the organic layer by minimal amount of water
  3. dry with materialDry the organic layer (combination of anhydrous MgSO4, Na2SO4 and K2CO3)
  4. concentrationconcentrate
  5. custompurify by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-825403d65f1d46b1995ee4f8846e3bde
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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