Glyoxylic Acid → 2-Hydroxy-6-chloroquinoxaline

HRID 1899915

Reaktionsgleichung

Reaktionsgleichung von HRID 1899915
[C:1]([OH:5])(=O)[CH:2]=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([NH2:14])[CH:8]=1>CO>[Cl:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:11][CH:12]=1)[NH:13][C:1](=[O:5])[CH:2]=[N:14]2

Komponenten

4

Edukt 2

HCID 760Glyoxylic AcidHCID 72634-Chloro-1,2-diaminobenzene

Produkt 1

HCID 755072-Hydroxy-6-chloroquinoxaline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Following the procedure of J. Med. Chem., 24, 93 (1981), glyoxylic acid (29.4 ml) is added to a solution of 4-chloro-1,2-phenylenediamine (38.0 g) and methanol (1.87 L) at 15°. The solution is stirred for 24 hr at 20°-25° and is concentrated. The residue is washed with water (4×608 ml), isopropanol (145 ml), and dried under reduced pressure to give a solid. Two successive recrystallizations from hot (ca 90°) 2-methoxyethanol (1.49 l and 0.927 l) gives the title compound, NMR (DMSO-d6) 12.55, 8.22, 7.86, 7.62 and 7.32 δ.

Aufarbeitung

  1. concentrationis concentrated
  2. washThe residue is washed with water (4×608 ml), isopropanol (145 ml)
  3. customdried under reduced pressure
  4. customto give a solid
  5. customTwo successive recrystallizations from hot (ca 90°) 2-methoxyethanol (1.49 l and 0.927 l)

Quellen und Nachweise

ORD-Eintrag
ord-15571a5f4db74fa883997e0502d293f6
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574038

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