3-Bromotoluene → HCID 22413424, compound

HRID 1721600Notes

Reaction equation

HRID 1721600 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[N:10]1[CH:15]=[CH:14][N:13]=[C:12]2[C:16]([O:18][C:19](=[O:20])[C:11]=12)=[O:17].[NH4+].[Cl-]>CCOCC.C1COCC1>[CH3:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:16]([C:12]1[C:11]([C:19]([OH:18])=[O:20])=[N:10][CH:15]=[CH:14][N:13]=1)=[O:17]

Participants

7

Reactant 4

HCID 115603-BromotolueneHCID 25517Ammonium ChlorideHCID 78482Furo(3,4-b)pyrazine-5,7-dioneHCID 5462224Magnesium

Product 1

HCID 22413424HCID 22413424, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent from 8.5 g (50 mmol) 3-bromotoluene and 1.2 g magnesium in 50 ml ether was added dropwise at 0°-10° C. to a solution of 7.5 g (50 mmol) pyrazine-2,3-dicarboxylic acid anhydride in 100 ml THF and after completed addition, the solution that formed was stirred for 4 hours at room temperature. 500 ml cold, saturated NH4Cl solution was then added, it was extracted with ethyl acetate and the organic phase was dried, concentrated by evaporation and purified as in example 1a and 2a. Yield 4 g (32% of theoretical yield).

Workup

  1. additionaddition
  2. customthe solution that formed
  3. extractionit was extracted with ethyl acetate
  4. customthe organic phase was dried
  5. concentrationconcentrated by evaporation
  6. custompurified as in example 1a and 2a
  7. customYield 4 g (32% of theoretical yield)

Sources & evidence

ORD record
ord-0d117d60d96a48f8ab0f1b80019f86bf
Source dataset
uspto-grants-1996_04
Patent number
US05512564

Reaction notes

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