Hydrochloric Acid → 6-Ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol

HRID 128626

Reaktionsgleichung

Reaktionsgleichung von HRID 128626
C([BH-](CC)CC)C.[Li+].[CH2:9]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[N:20][C:21]=1[CH3:22])[N:18]=[CH:17][C:16]([C:23](OCC)=[O:24])=[C:15]2[NH:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH3:10].Cl.O>C1COCC1>[CH2:9]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[N:20][C:21]=1[CH3:22])[N:18]=[CH:17][C:16]([CH2:23][OH:24])=[C:15]2[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH3:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9907935Ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylateHCID 23664628Lithiumtriethylborohydride2×

Produkt 1

HCID 193742646-Ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium triethylborohydride (a 1M solution in THF, 47 ml) was added to a solution of ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate (4.5 g) in THF (150 ml) with stirring under nitrogen at 0°-10° C. The mixture was allowed to warm up to ambient temperature and stirred at this temperature for 18 hours. Further lithium triethylborohydride solution (15 ml) was added and the solution stirred at ambient temperature for 4 hours. The reaction mixture was cooled to 5° C. and then 5M hydrochloric acid (5 ml) was added carefully followed by water (50 ml). The organic layer was separated and the aqueous layer extracted with ether. The aqueous layer was basified with 5M sodium hydroxide solution and extracted into ethyl acetate. The residue, obtained from the ethyl acetate extracts, was purified by flash chromatography on silica, using dichloromethane/IMS (15/1) as the mobile phase, to give 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridin-3-ylmethanol, m.p. 193°-197° C.

Aufarbeitung

  1. stirringstirred at this temperature for 18 hours
  2. stirringthe solution stirred at ambient temperature for 4 hours
  3. temperatureThe reaction mixture was cooled to 5° C.
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ether
  6. extractionextracted into ethyl acetate
  7. customThe residue, obtained from the ethyl acetate extracts
  8. customwas purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-560a97bfc68242c4acf9af5ea9b09111
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464781

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