HCID 57456934, Verbindung → 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
Reaktionsgleichung
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15]CC1C=CC=CC=1)=[O:14]>CN(C=O)C.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([OH:15])=[O:14]Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Benzyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 66a) (0.6 g, 2.04 mmol) was dissolved in DMF (8 mL) and heated at 70° C. under a hydrogen balloon in the presence of 10% Pd/C (0.15 g) for 1 hour. The Pd/C was filtered out and washed with dichloromethane and the solvents were removed under vacuum. The residue was dissolved/suspended in NaOH (2M, 40 mL), stirred at room temperature for 30 minutes and the solution washed with dichloromethane. The aqueous layer was cooled to 0° C. and acidified to pH 1 with 2M HCl. The resultant precipitate was collected and washed with dichloromethane to give 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (0.050 g, 12%) as a light yellow solid. M.p.: >250° C. 1H NMR (400 MHz, DMSO-d6) δ 7.32 (m, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.69 (m, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.86 (s, 1H), 9.87 (s, 1H), 11.95 (s, 1H). MS 205 (MH+).
Aufarbeitung
- filtrationThe Pd/C was filtered out
- washwashed with dichloromethane
- customthe solvents were removed under vacuum
- washthe solution washed with dichloromethane
- temperatureThe aqueous layer was cooled to 0° C.
- customThe resultant precipitate was collected
- washwashed with dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-c67e11e763dc4f1a86b20aecd6b0dc3c
- Quelldatensatz
- uspto-grants-2014_01
- Patentnummer
- US08633186B2
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