Water → 5-Bromoquinoline-8-carboxylic acid
Reaktionsgleichung
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Br:7][C:8]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[OH2:19]>N1C=CC=CC=1>[Br:7][C:8]1[CH:17]=[CH:16][C:15]([C:18]([OH:2])=[O:19])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
A solution of potassium permanganate (18.2 g, 115.5 mmol, 2 equiv) in H2O (200 mL) was added to a hot (110° C.) solution of 5-bromo-8-methyl-quinoline (Step 159.4) (12.8 g, 57.7 mmol) in pyridine (120 mL). The reaction mixture was stirred for 10 min at 110° C. and filtered while hot. The residue in the filter was washed with H2O and pyridine. The filtrate was concentrated to remove pyridine, diluted with Et2O and basified by addition of a 2 N aqueous solution of NaOH (20 mL). The aqueous layer was separated and made acidic (pH 3) by addition of a 2 N aqueous solution of HCl. The resulting precipitate was collected by vacuum filtration to provide 1.45 g of the title compound as a green solid: ESI-MS: 251.9/253.9 [M+H]+; tR=3.56 min (System 1).
Aufarbeitung
- filtrationfiltered while hot
- washThe residue in the filter was washed with H2O and pyridine
- concentrationThe filtrate was concentrated
- customto remove pyridine
- additiondiluted with Et2O
- additionbasified by addition of a 2 N aqueous solution of NaOH (20 mL)
- customThe aqueous layer was separated
- additionby addition of a 2 N aqueous solution of HCl
- filtrationThe resulting precipitate was collected by vacuum filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-4743d1afdac74a1994b06a3c43907bbd
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536175B2
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