2-[2-Chloro-5-(methoxycarbonyl)phenylamino]-2-butenedioic acid diethyl ester → 8-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

HRID 1091450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091450
[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:14]=1[Cl:23])=[CH:6][C:7]([O:9]CC)=O)[CH3:2]>C1(C2C=CC=CC=2)C=CC=CC=1.CCOCC>[CH3:22][O:21][C:19]([C:17]1[C:18]2[C:7](=[O:9])[CH:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])[NH:12][C:13]=2[C:14]([Cl:23])=[CH:15][CH:16]=1)=[O:20]

Komponenten

3

Edukt 1

HCID 589597002-[2-Chloro-5-(methoxycarbonyl)phenylamino]-2-butenedioic acid diethyl ester

Produkt 1

HCID 589596858-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 665887421,1'-Biphenyl;ethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

A suspension of 23 (9.00 g, 25.4 mmol) in biphenyl ether (100 mL) was heated to 250° C. and stirred for 3 h. Then the reaction mixture was cooled to room temperature and purified by flash chromatography (hexanes to EtOAc) to afford a colorless oil (24, 3.88 g, 49.4%). 1H NMR (CDCl3, 300 MHz) δ 9.39 (br s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 6.96 (s, 1H), 4.54 (q, J=7.0 Hz, 2H), 4.00 (s, 3H), 1.46 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. custompurified by flash chromatography (hexanes to EtOAc)
  3. customto afford a colorless oil (24, 3.88 g, 49.4%)

Quellen und Nachweise

ORD-Eintrag
ord-4cbcfcad43c640b69658bb3dc8e69850
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129382B2

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