Water → 3-(4,6-Dimethoxypyrimidine-2-yl)-2-methylindole

HRID 492126

Reaktionsgleichung

Reaktionsgleichung von HRID 492126
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12](=O)[CH3:13])[N:4]=1.[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:21][C:12]=2[CH3:13])[N:4]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 8857Ethyl AcetateHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

Produkt 1

HCID 129793683-(4,6-Dimethoxypyrimidine-2-yl)-2-methylindoleAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In 10 ml of toluene were dissolved 1.61 g (8.2 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 1.08 g (10 m moles) of phenylhydrazine. Thereto was added 1.36 g (10 m moles) of zinc chloride, followed by refluxing for 1 hour. The reaction mixture was allowed to cool, and ethyl acetate and water were added to dissolve the whole reaction mixture. The oily layer was washed with water, separated and dried over Glauber's salt. The resulting oily layer was concentrated under reduced pressure to obtain an orange solid. The solid was recrystallized from methanol to obtain 1.37 g (5.1 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2-methylindole. Yield: 62% Melting point: 182 to 184° C.

Aufarbeitung

  1. temperatureby refluxing for 1 hour
  2. temperatureto cool
  3. dissolutionto dissolve
  4. customthe whole reaction mixture
  5. washThe oily layer was washed with water
  6. customseparated
  7. dry with materialdried over Glauber's salt
  8. concentrationThe resulting oily layer was concentrated under reduced pressure
  9. customto obtain an orange solid
  10. customThe solid was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-06005b90c1984639ab138f7e6937a925
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531654B2

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