Dimethylformamide → 4-Chloro-7-methoxycinnoline hydrochloride

HRID 7485

Reaktionsgleichung

Reaktionsgleichung von HRID 7485
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-6d4c3752ba7f4c5eae803cc519e25ef9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087602B2

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