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Methanol → 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]amino]-3,5-dimethyl-benzoic acid

HRID 239981
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 239981
[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:19]=[C:18]([C:20]([NH:22][C:23]3[C:32]([CH3:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][C:24]=3[CH3:34])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:19]=[C:18]([C:20]([NH:22][C:23]3[C:24]([CH3:34])=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][C:32]=3[CH3:33])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH2:9]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707365Methyl 4-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]Amino]-3,5-dimethyl-benzoate

Produkt 1

HCID 867073664-[[2-(4-Hydroxy-1-Piperidyl)Quinoline-4-carbonyl]amino]-3,5-dimethyl-benzoic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of methyl 4-(2-(4-hydroxypiperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate (0.13 g, 0.0003 mol) in THF:MeOH (5 ml:2 ml). After 5 h at 50° C., the organic solvent is removed under reduced pressure and the residue is diluted with water acidified to pH 6 with aqueous 1N HCl and extracted with ethyl acetate (2×20 ml). The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with pentane and diethyl ether and filtered to afford the title compound as a light yellow solid (0.05 g, 40%). Mass spectrum (m/z): 420.2 (M+1).

Aufarbeitung

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with pentane and diethyl ether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-b31e6d132dd6403ab5dbf62753b5812e
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642768B2

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