Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate → HCID 178469656, Verbindung

HRID 1841526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1841526
[C:1]([O:4][CH2:5][C:6]1[CH:24]=[CH:23][C:9]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([I:25])[CH:7]=1)(=[O:3])[CH3:2]>O(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:24]=[C:23]2[C:9](=[C:8]([I:25])[CH:7]=1)[N:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]2[OH:20])(=[O:3])[CH3:2]

Komponenten

3

Edukt 1

HCID 22724556Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate

Produkt 1

HCID 178469656HCID 178469656, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

A solution of diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate (1.75 g) in Ph2O (20 mL) is heated at 250° C. for 40 min. The reaction is cooled to room temperature and diluted with hexanes. The resulting solid is collected and dried. The crude solid is adsorbed onto silica and chromatographed (Biotage flash 40S, gradient from CH2Cl2 to 2% MeOH/CH2Cl2). Product containing fractions are combined and concentrated to yield 0.98 g (62%) of ethyl 6-[(acetyloxy)methyl]-4-hydroxy-8-iodo-3-quinolinecarboxylate, m.p. 119-123° C.

Aufarbeitung

  1. customThe resulting solid is collected
  2. customdried
  3. customchromatographed (Biotage flash 40S, gradient from CH2Cl2 to 2% MeOH/CH2Cl2)
  4. additionProduct containing fractions
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7c42c9579730492294b0f84fe6defa9d
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06683181B2

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