Potassium Hydroxide → HCID 86732795, Verbindung

HRID 525927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525927
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:46])[C:5]([C:34]([O:36]CC1C=CC(OC)=CC=1)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33].[OH-].[K+]>CO.O>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:46])[C:5]([C:34]([OH:36])=[O:35])=[N:6][N:7]2[CH2:32][CH3:33]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 86732794HCID 86732794, Verbindung

Produkt 1

HCID 86732795HCID 86732795, VerbindungAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To the solution of 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (24 g, 37.2 mmol) in methanol (400 mL) and water (133 mL) was added potassium hydroxide (8.35 g, 149 mmol). The reaction mixture was heated to reflux for 3 h. Solvent was removed under vacuum. The residue was suspended in water and the resulting mixture was acidified to pH4 with 2N hydrochloric acid. The precipitated solid was filtered and dried to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (12.6 g, 24.00 mmol, 64.5% yield). LCMS: (M+H)+: 525.2

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. customSolvent was removed under vacuum
  4. filtrationThe precipitated solid was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a6068a94f2c54e33acaf161457cf625a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340556B2

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