Isopropanol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline

HRID 1057333

Reaktionsgleichung

Reaktionsgleichung von HRID 1057333
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[CH:23][C:21]=1[NH2:22].C(O)(C)C>CC(O)CCC>[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[CH:23][C:21]=1[NH:22][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 107070484-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline

Produkt 1

HCID 116176914-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 223862-PentanolLösungsmittel

Versuchsvorschrift

A suspension of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.2 g, 0.74 mmol), (prepared as described for the starting material in Example 2), and 2-fluoro-5-hydroxy-4-methylaniline (126 mg 0.89 mmol) in 2-pentanol (2.5 ml) was heated at reflux for 7.5 hours. After cooling, isopropanol was added and the solid was filtered off, washed with isopropanol and ether, and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline as the hydrochloride salt (yellow solid 196 mg, 64%).

Aufarbeitung

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 7.5 hours
  4. temperatureAfter cooling
  5. filtrationthe solid was filtered off
  6. washwashed with isopropanol and ether
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d207cd6679404fa1a48069c27a7dc65e
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514971B1

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