Triphenylphosphine → 3-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester

HRID 1422912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422912
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4].[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CO.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:21])[C:13]=2[F:15])[N:8]=[CH:7][C:6]=1[O:17][C:18](=[O:20])[CH3:19])=[O:4]

Komponenten

7

Edukt 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 672473533-Acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester

Produkt 1

HCID 672479353-Acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl esterAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanol (0.52 mL, 12.72 mmol, 3.0 eq) is added at room temperature to a stirred solution of 3-acetoxy-5-fluoro-6-hydroxy-quinoline-4-carboxylic acid methyl ester (1.18 g, 4.24 mmol, 1.0 eq) in tetrahydrofuran (50 mL), followed by triphenylphosphine (2.22 g, 12.72 mmol, 3.0 eq) and diethyl azodicarboxylate (1.48 g, 12.72 mmol, 3.0 eq). After 3 hours stirring at room temperature, solvent is evaporated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 30:1, v/v) to afford 3-acetoxy-5-fluoro-6-methoxy-quinoline-4-carboxylic acid methyl ester as a yellow oil (0.81 g, 65% yield).

Aufarbeitung

  1. customsolvent is evaporated
  2. customto give a crude product that
  3. customis purified by column chromatography (silica gel, eluent

Quellen und Nachweise

ORD-Eintrag
ord-1adfdf1fdb8c4b6683baf0cc579169ef
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927541B2

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