Water → 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline

HRID 749060

Reaktionsgleichung

Reaktionsgleichung von HRID 749060
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1.[Cl:32][CH2:33][CH2:34][CH2:35]Br.[O-]CCCC.[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][C:6]1[CH:27]=[CH:26][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:35][CH2:34][CH2:33][Cl:32])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:24]#[N:25])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 23699084Potassium butoxideHCID 1358198314-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline

Produkt 1

HCID 220485174-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The product of step 2 (206.5 mg, 0.5 mmole) and 1-chloro-3-bromopropane (95 mg, 0.6 mmole) was dissolved in dimethylsulphoxide (5 ml) in the presence of potassium butoxide (0.55 ml, 11.0M in THF, 0.55 mmole) in and the mixture held at room temperature for 18 hours. Water was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and brine then dried (MgSO4) and evaporated to give 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(3-chloropropoxy)quinoline, intermediate 1, (189 mg, 77%) as a yellow gum.

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialthen dried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d0286c75557a404eba88c05721252874
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402583B2

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