Toluene → HCID 22646629, Verbindung

HRID 393636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393636
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[NH:9][CH:8]=[CH:7][C:6]2=O.C1(C)C=CC=CC=1.S(Cl)([Cl:32])=O>CN(C=O)C>[ClH:32].[Cl:32][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 226466186-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinone

Produkt 1

HCID 22646629HCID 22646629, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

A solution of 6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1,4-dihydroquinolin-4-one (950 mg, 3.1 mmol) in thionyl chloride (25 ml) containing DMF (10 drops) was heated at reflux for 1.5 hours. After cooling, toluene was added and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinoline hydrochloride (1.23 g, 100%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customthe volatiles were removed by evaporation
  5. customThe residue was triturated with ether
  6. filtrationcollected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a1c3a9ed46084622b5826ae5b564405e
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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