Ethyl bromopyruvate → 1,2-Dicarbethoxypyrrolo[1,2-c]quinazoline

HRID 65927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65927
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:12][CH:11]=1.C(=O)(O)[O-].[Na+]>CCO>[C:4]([C:3]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][N:12]2[C:2]=1[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:19]=1[N:10]=[CH:11]2)([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 22756349Ethyl Quinazoline-4-acetate

Produkt 1

HCID 227563371,2-Dicarbethoxypyrrolo[1,2-c]quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl bromopyruvate (8.0 g, 0.1041 m) and ethyl 4-quinazolylacetate prepared according to the procedure of Elderfield and Serlin, J. Org. Chem. 16, 1669 (1951) (2.32 g, 0.011 m) in dry EtOH (250 ml) was heated at reflux for 24 hr. Sodium bicarbonate was added until effervescence ceased. A solid formed and this was filtered, washed well with H2O, and dried. The crude product (1.8 g) was chromatographed on 150 g of Silicar. The desired product was eluted with 3% EtOAc/benzene. Crystallization from MeOH afforded the desired product as a white solid; m.p. 125°-126° C.

Aufarbeitung

  1. temperatureat reflux for 24 hr
  2. customA solid formed
  3. filtrationthis was filtered
  4. washwashed well with H2O
  5. customdried
  6. customThe crude product (1.8 g) was chromatographed on 150 g of Silicar
  7. washThe desired product was eluted with 3% EtOAc/benzene
  8. customCrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-a3ffbe93a90740d3a2e3f2287da1359f
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04129653

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