Hydrochloric Acid → 2-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

HRID 2423316

Reaktionsgleichung

C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[OH:29].Cl>CS(C)=O.CCOC(C)=O.O>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][C:28]=1[O:29][C:8]1[C:9]([N+:18]([O-:20])=[O:19])=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Cs2CO3 (15.5 g, 47.5 mmol) was added to (24.1) (3 g, 14.4 mmol) and 3-methoxy-4-hydroxyphenylacetic acid (2.63 g, 14.4 mmol) in DMSO (30 mL) at room temperature. The mixture was then stirred at 80° C. for 4 h. After cooling, the reaction mixture was treated with water (50 mL), 3N HCl (35 mL) and EtOAc (100 mL). The product was insoluble in EtOAc, but stayed in the organic layer. So the organic layer was washed with water 4 times to get rid of all the salts, and the organic layer was separated, concentrated and dried under vacuum to afford 24.2. MS ESI (pos.) m/z: 355.1 (M+H). 1H NMR (DMSO-d6) δ 8.99 (dd, 1H); 8.24 (m, 2H); 7.77 (dd, 1H); 7.29 (d, 1H); 7.21 (d, 1H); 7.18 (d, 1H); 6.96 (dd, 1H); 3.73 (s, 3H); 3.65 (s, 2H).

Aufarbeitung

temperatureAfter cooling
washSo the organic layer was washed with water 4 times
customto get rid of all the salts
customthe organic layer was separated
concentrationconcentrated
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-16d0c3b2ffd34074ae81e23fc3d08fa6
Quelldatensatz: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07960567B2

Verknüpfte Notizen

Wird geladen…