Acetic Anhydride → 2-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)benzoic acid

HRID 1468575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468575
C([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])/[CH:12]=[CH:13]\[C:14]([OH:16])=O)=[CH:6][CH:5]=1)(O)=O.[C:18]([O:21]C(=O)C)(=[O:20])C.C([O-])(=O)C.[Na+]>>[O:16]=[C:14]1[CH:13]=[CH:12][C:11](=[O:17])[N:10]1[C:7]1[C:6]([C:18]([OH:21])=[O:20])=[CH:5][CH:4]=[CH:9][CH:8]=1

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 5717537(Z)-4-(3-carboxyacrylamido)benzoic acid

Produkt 1

HCID 2485962-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)benzoic acidAusbeute 33 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-(4-carboxyphenyl)maleamic acid (5.0 g, 21.2 mmol), acetic anhydride (4 ml, 42.5 mmol) and sodium acetate (3.48 g, 42.5 mmol) Was heated at 80° C. for 3h. After heating, excess acetic anhydride was removed under reduced pressure and the residue purified by column chromatography using 0-4%. MeOH/DCM as an eluent to give 3k (33%) as a solid.15 mp: 165-168° C.; 1H NMR (400 MHz, DMSO-d6): δ 7.20 (s, 2H), 7.47 (d, J=8.4 Hz, 2H), 8.02 (d, 8.0 Hz, 2H), 12.75 (brs, 1H); HRMS (m/z): [M−H]− calcd for C11H6NO4, 216.0302; found, 216.0296.

Aufarbeitung

  1. temperatureAfter heating
  2. customexcess acetic anhydride was removed under reduced pressure
  3. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e1d5d1efe01d45d8a2199a1cc494359a
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09005670B2

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