Dimethylformamide → 7-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

HRID 1057326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057326
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[CH:14][N:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)([Cl:29])=O>>[ClH:29].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:29])=[CH:14][N:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178418820HCID 178418820, Verbindung

Produkt 1

HCID 219910077-Benzyloxy-4-chloro-6-methoxycinnoline hydrochloride

Versuchsvorschrift

The starting material, 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride, was obtained by heating a solution of 7-benzyloxy-4-hydroxy-6-methoxycinnoline (11 g, 39 mmol) in thionyl chloride (180 ml) containing DMF (1 ml) at reflux for 1 hour. After cooling, excess thionyl chloride was removed by evaporation and azeotroped with toluene. The residue was triturated with ether, filtered off, washed with ether and dried under vacuum to give 7-benzyloxy-4-chloro-6-methoxycinnoline hydrochloride as a cream solid (13.6 g, quantitative).

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. temperatureAfter cooling
  3. customexcess thionyl chloride was removed by evaporation
  4. customazeotroped with toluene
  5. customThe residue was triturated with ether
  6. filtrationfiltered off
  7. washwashed with ether
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5e20807965fb44c39946f8651bfce1d7
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514971B1

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