Water → 3-(4,6-Dimethoxypyrimidine-2-yl)-2,7-dimethylindole

HRID 1785380

Reaktionsgleichung

Reaktionsgleichung von HRID 1785380
[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.Cl.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23]N.C(OCC)(=O)C.O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2[C:19]3[C:18](=[C:17]([CH3:16])[CH:22]=[CH:21][CH:20]=3)[NH:23][C:12]=2[CH3:13])[N:4]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

Produkt 1

HCID 129793703-(4,6-Dimethoxypyrimidine-2-yl)-2,7-dimethylindoleAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 1140TolueneLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

In 20 ml of toluene were dissolved 0.77 g (3.9 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone and 0.69 g (4.3 m moles) of 2-methylphenylhydrazine hydrochloride. Thereto was added 0.64 g (4.7 m moles) of zinc chloride, followed by refluxing for 2 hours. The reaction mixture was allowed to cool, and then 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 using a rotary evaporator, to obtain an orange solid. The solid was treated with ethyl acetate/n-hexane to obtain 0.38 g (1.34 m moles) of 3-(4,6-dimethoxypyrimidine-2-yl)-2,7-dimethylindole. Yield: 34% Melting point: 145 to 147° C.

Aufarbeitung

  1. temperatureby refluxing for 2 hours
  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. customa rotary evaporator
  10. customto obtain an orange solid

Quellen und Nachweise

ORD-Eintrag
ord-1a9c4ecc38a444a3819090779b3e6868
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504503B2

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