Water → 8-(2,6-Dichlorobenzoylamino)-3-hydroxymethylquinoline

HRID 613485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613485
C([O:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])(=O)C.[OH-].[Na+].O>O1CCOCC1.CN(C)C=O>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[C:17]([NH:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:15]2)=[O:26]

Komponenten

6

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 195927753-Acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline

Produkt 1

HCID 195922958-(2,6-Dichlorobenzoylamino)-3-hydroxymethylquinolineAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3-acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (25.9 mg), 1N sodium hydroxide solution (0.24 ml) in dioxane and dimethylformamide (4 drops) was stirred for 2 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate-n-hexane to give 8-(2,6-dichlorobenzoylamino)-3-hydroxymethylquinoline (20 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-59c3adddf5d241c29175a9b440531623
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008230

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