Methanol → 1-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione

HRID 1494349

Reaktionsgleichung

Reaktionsgleichung von HRID 1494349
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])([OH:3])=[O:2].[CH3:17]O.S(=O)(=O)(O)O>O>[CH3:17][O:2][C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])=[O:3]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid

Produkt 1

HCID 129386651-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dioneAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1.0 g (4.5 mmol) 1-carboxymethylquinoxaline-2,3(1H,4H)-dione, 15 ml dry methanol and 0.2 ml concentrated sulfuric acid was stirred at 80° C. for 1 h. After cooling to 25° C. the reaction mixture was poured in water and made alkaline. The precipitate was filtered off and recrystallized (acetone) to give 0.22 g (21%) 1-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione. M.p. 269° C. 1H-NMR (DMSO-d6): 12.0 (1H, broad s), 7.1 (4H, s), 4.9 (2H, s), 3.7 (3H, s).

Aufarbeitung

  1. temperatureAfter cooling to 25° C. the reaction mixture
  2. filtrationThe precipitate was filtered off
  3. customrecrystallized (acetone)

Quellen und Nachweise

ORD-Eintrag
ord-24b9dfca1e2447f88ee920624a8b4b4a
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026704

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