Ethyl bromopyruvate → Ethyl pyrrolo[1,2-c]quinazoline-2-carboxylate

HRID 65920Notes

Reaction equation

HRID 65920 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][N:12]=1>C(O)C>[C:4]([C:3]1[CH:10]=[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][N:12]2[CH:2]=1)([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvate2×HCID 2415204-Methylquinazoline

Product 1

HCID 4407258Ethyl pyrrolo[1,2-c]quinazoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl bromopyruvate (3.2g, 0.016 m) and 4-methylquinazoline (2.0g, 0.014 m) in dry ethanol (150 ml) was heated at reflux for two hours. During this time, a tan solid formed. Excess ethyl bromopyruvate was added (1.0g) and the reaction mixture was allowed to reflux overnight. After this time, the reaction was complete. The alcohol was removed in vacuo and the residue diluted with H2O. Sodium bicarbonate was added until effervescence ceased and the aqueous mixture extracted with ether. The ether extracts were combined, dried over Na2SO4, filtered and the solvent removed in vacuo to yield a tan solid. Crystallization from MeOH afforded the product as a white solid; m.p. 138°-139° C.

Workup

  1. temperatureat reflux for two hours
  2. customDuring this time, a tan solid formed
  3. temperatureto reflux overnight
  4. customThe alcohol was removed in vacuo
  5. additionthe residue diluted with H2O
  6. additionSodium bicarbonate was added until effervescence
  7. extractionthe aqueous mixture extracted with ether
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customto yield a tan solid
  12. customCrystallization from MeOH

Sources & evidence

ORD record
ord-9361542a45ab4ce0a416dd3c4d075d1d
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

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