Hydrochloric Acid → Ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate
Reaktionsgleichung
[CH:1](=[N:8][N:9]([C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20](OC)=[O:21])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].O.Cl>C(O)C>[OH:21][C:20]1[C:19]2[C:18](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]([N:8]=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10](=[O:17])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
The product of Example 226B (5.17 g, 14.59 mmol) in ethanol (100 mL) was reacted with sodium ethoxide (21% by weight in ethanol, 5.50 mL, 14.60 mmol) at 25° C. then heated at 50° C. for 1 hour. After cooling to 25° C., the reaction mixture was poured into water, acidified to pH 4 with 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum to give the title compound (4.51 g, 96%). MS (DCI) m/z 323 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.73 (s, 3 H) 7.21 (m, 1 H) 7.56 (m, 5 H) 7.95 (m, 2 H) 8.03 (d, J=7.72 Hz, 1 H) 9.08 (s, 1 H).
Aufarbeitung
- temperatureAfter cooling to 25° C.
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- customthe solvent removed under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-8de1a9a4ad7342ccba2d7011c3d62393
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07902203B2
Notizen zur Reaktion
Wird geladen…