5-Amino-4-fluoro-2-methylphenol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6,7-dimethoxycinnoline

HRID 7499

Reaktionsgleichung

Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[F:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH2:20]>CC(O)CCC>[F:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH:20][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A solution of 4-chloro-6,7-dimethoxycinnoline hydrochloride (261 mg, 1 mmol), (prepared as described for the starting material in Example 1), and 2-fluoro-5-hydroxy-4-methylaniline (170 mg, 1.2 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (5 ml) was heated at 120° C. for 3 hours. After cooling, the solid was filtered off, washed with isopropanol and ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6,7-dimethoxycinnoline as an hydrochloride salt (301 mg, 82%).

Aufarbeitung

custom(prepared
temperatureAfter cooling
filtrationthe solid was filtered off
washwashed with isopropanol and ether
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-f2a6c961afe74bd9b766dbe37ed3ddaf
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087602B2

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