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Methanol → 4-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

HRID 2213723
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2213723
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:31]#[N:32].CO>CN(C=O)C.O.C(OCC)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13]1[C:22]2[C:17](=[CH:18][C:19]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=3[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:31]#[N:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 887MethanolHCID 111232,4-DichloroanilineHCID 24758Sodium hydrideHCID 99441164-Chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile

Produkt 1

HCID 102959004-(2,4-Dichloroanilino)-7,8-dimethoxybenzo[g]quinoline-3-carbonitrileAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 178.2 mg (1.1 mmol) of 2,4-dichloroaniline and 44.0 mg (1.1 mmol) of sodium hydride in anhydrous DMF is stirred at room temperature for 0.5 hours. To the mixture is added 149.4 mg (0.5 mmol) of 4-chloro-7,8-dimethoxybenzo[g]quinoline-3-carbonitrile. The resulting mixture is heated at 50–60° C. for 1 hour. After cooling, the mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate. Removal of the solvent yields a dark residue which is purified on preparative TLC (developing solvent: 97:3 methylene chloride/methanol), giving a yellow foam. Trituration of the foam with diethyl ether containing several drops of methanol yields 126.1 mg (59.5%) of the product as a yellow solid, mp 271–273° C.

Aufarbeitung

  1. temperatureThe resulting mixture is heated at 50–60° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent
  7. customyields a dark residue which
  8. customis purified on preparative TLC (developing solvent: 97:3 methylene chloride/methanol)
  9. customgiving a yellow foam

Quellen und Nachweise

ORD-Eintrag
ord-985c6933486047f2b25b1ae25e6a339d
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07105531B2

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