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

HRID 1060596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060596
[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 CH2CI2 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 CH2CI2 to 2% MeOH/CH2Cl2)
  4. additionProduct containing fractions
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3fac58c96f704743b64d40026b37243d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525049B2

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