Hydrochloric Acid → 6-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acid

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Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][N:23]=1.Cl>O.CS(C)=O>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][N:23]=[C:22]2[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

6-Hydroxy-1-naphthoic acid (1.43 g, 7.6 mmol) and 38 ml of DMSO were stirred at room temperature while cesium carbonate (7.5 g, 22.9 mmol) and 4-chloro-6,7-dimethoxy-quinazoline (2.05 g, 9.14 mmol) were added. The mixture was heated at 140° C. for 3 hours. The mixture was cooled to room temperature and diluted with 40 mL of H2O. The mixture was neutralized with 2 N HCl to 6.5. The deposited solids were collected by vacuum filtration, washed with H2O, dried under vacuum and recrystallized from methanol to give the title compound (1.68 g, 59% yield) as a brown solid. LC-MS (m/z) 377 (M+1).

Aufarbeitung

additionwere added
temperatureThe mixture was cooled to room temperature
filtrationThe deposited solids were collected by vacuum filtration
washwashed with H2O
customdried under vacuum
customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag: ord-371a6b1d00c446ae95c057e355967091
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08211901B2

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