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

HRID 65927Notes

Reaction equation

HRID 65927 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a3ffbe93a90740d3a2e3f2287da1359f
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

Loading…