Oxalic acid dihydrate → 6-Chloro-1-methylquinoxaline-2,3(1H,4H)-dione

HRID 1709213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1709213
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.O.O.[C:15]([OH:20])(=O)[C:16](O)=[O:17]>C(O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH3:9])[C:16](=[O:17])[C:15](=[O:20])[NH:10]2

Komponenten

5

Edukt 2

HCID 61373Oxalic acid dihydrateHCID 27368364-chloro-N-methyl-2-nitroaniline

Produkt 1

HCID 32931736-Chloro-1-methylquinoxaline-2,3(1H,4H)-dioneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 4-chloro-1-methylamino-2-nitrobenzene (1.73 g, 9.3 mmol) in 50 ml of ethanol was hydrogenated at room temperature and 2 atm. pressure in the presence of 5% palladium-on-carbon (0.5 g) until the theoretical amount of hydrogen was absorbed. The catalyst was filtered off, and 50 ml of IN hydrochloric acid was added to the filtrate. The acidic filtrate was evaporated to dryness and the solid residue was refluxed with oxalic acid dihydrate (1.4 g, 11 mmol) in 100 ml of 4M hydrochloric acid for 90 min. The mixture was cooled and the precipitated product was collected by filtration and washed with water, ethanol and ether to give 0.45 g (23%) of the title compound. M.p. 341.5° C. (N,N-dimethylformamide); IR (KBr): 1700, 1660 cm-1, 1H-NMR (DMSO-d6 : 3.43 (s, 3H, CH3), 6.97-7.40 (m, 3H, ArH), 12.0 (broad s, 1H, NH); MS m/z: 212 (M+ +2, 50%), 210 (M+, 100%).

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. custom2 atm. pressure in the presence of 5% palladium-on-carbon (0.5 g) until the theoretical amount of hydrogen was absorbed
  3. filtrationThe catalyst was filtered off
  4. addition50 ml of IN hydrochloric acid was added to the filtrate
  5. customThe acidic filtrate was evaporated to dryness
  6. temperatureThe mixture was cooled
  7. filtrationthe precipitated product was collected by filtration
  8. washwashed with water, ethanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-13bd3ee29e14429297436e0fe7022926
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04948794

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