Dimethylformamide → 4-Chloro-7-methoxycinnoline hydrochloride

HRID 1057339

Reaktionsgleichung

Reaktionsgleichung von HRID 1057339
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:21])=O>>[ClH:21].[Cl:21][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[N:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418974HCID 178418974, Verbindung

Produkt 1

HCID 219910204-Chloro-7-methoxycinnoline hydrochlorideAusbeute 97 %

Versuchsvorschrift

The starting material 4-chloro-7-methoxycinnoline hydrochloride was obtained by heating a solution of 4-hydroxy-7-methoxycinnoline (352 mg, 2 mmol), (prepared as described in J. Chem. Soc. 1955, 2100), in thionyl chloride (3.5 ml) containing DMF (20 μl) at reflux, for 1 hour. After removing excess thionyl, chloride by evaporation and azeotroping with toluene. The residue was triturated with ether, filtered off and washed with ether to give 4-chloro-7-methoxycinnoline hydrochloride as a yellow solid (450 mg, 97%).

Aufarbeitung

  1. temperatureat reflux, for 1 hour
  2. customAfter removing excess thionyl, chloride
  3. customby evaporation
  4. customazeotroping with toluene
  5. customThe residue was triturated with ether
  6. filtrationfiltered off
  7. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-56cabee775524ef88048e4fa63f70c35
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514971B1

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