Boron tribromide → Diethyl (6-hydroxy-3-quinolyl)methylacetamidomalonate

HRID 477710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477710
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][CH2:14][C:15]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([CH2:13][CH2:14][C:15]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])=[CH:6]2

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 57184951Diethyl (6-methoxy-3-quinolyl)methylacetamidomalonate

Produkt 1

HCID 57234501Diethyl (6-hydroxy-3-quinolyl)methylacetamidomalonateAusbeute 11,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 0.39 g (1 mmol) of diethyl (6-methoxy-3-quinolyl)methylacetamidomalonate in 10 mL of dry methylene chloride was added dropwise at -70° C. a 1 M solution of boron tribromide in methylene chloride. The reaction temperature was gradually raised to room temperature while stirring overnight. Then, the reaction mixture was poured into ice water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel, using 1:1 ethyl acetate/methylene chloride and then ethyl acetate as eluents, to give 43 mg (11.5%) of the desired product as a solid. TLC Rf =0.46 (ethyl acetate); NMR (CDCl3) δ 8.4 (1H, bs), 7.95 (1H, d), 7.7 (1H, bs), 7.35 (1H, dd), 7.1 (1H, d), 6.8 (1H, bs), 4.25 (4H, m), 3.8 (2H, bs), 2.0 (3H, s), 1.3 (6H, m); IR (KBr) ν 3700-2800, 1740, 1660, 1645, 1620, 1500 cm-1. The product has the structural formula: ##STR105##

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8ad3c82df46a48c99e7ee41ea97d3e16
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888427

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