P-Anisidine → Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

HRID 1956429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956429
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]2[NH:25][C:24]1[CH:26]=[CH:27][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 7732P-Anisidine2×HCID 11430Potassium Carbonate2×HCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

Produkt 1

HCID 23209166Ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate (1.68 g), 4-methoxyaniline (0.78 g), dry THF (50 ml) and anhydrous potassium carbonate (1.74 g) was stirred at ambient temperature for 7 hours. Further amounts of 4-methoxyaniline (0.4 g) and anhydrous potassium carbonate (0.9 g) were added and the mixture stirred at ambient temperature for 32 hours. The mixture was evaporated to dryness and the residue diluted with water (100 ml). The mixture was extracted into dichloromethane to give an oil which solidified. The solid was purified by column chromatography on silica using ethyl acetate as the mobile phase to give ethyl 6-methoxy-4-(4-methoxyanilino)-1,5-naphthyridine-3-carboxylate, m.p. 115°-117° C.

Aufarbeitung

  1. stirringthe mixture stirred at ambient temperature for 32 hours
  2. customThe mixture was evaporated to dryness
  3. additionthe residue diluted with water (100 ml)
  4. extractionThe mixture was extracted into dichloromethane
  5. customto give an oil which
  6. customThe solid was purified by column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-c6946770221947b9b3867228578e2fa6
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780482

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