Hydrochloric Acid → 1-(Methoxycarbonylmethyl)-7-(2,5-dimethyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 1458818Notes

Reaction equation

HRID 1458818 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])[NH:14][C:13](=[O:22])[C:12](=[O:23])[NH:11]3)[C:4]([CH3:7])=[CH:5][CH:6]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31]C)=[O:29].Cl>CN(C)C=O>[CH3:31][O:30][C:28]([CH2:27][N:11]1[C:10]2[C:15](=[CH:16][C:17]([C:18]([F:21])([F:20])[F:19])=[C:8]([N:3]3[C:4]([CH3:7])=[CH:5][CH:6]=[C:2]3[CH3:1])[CH:9]=2)[NH:14][C:13](=[O:22])[C:12]1=[O:23])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 220971586-(2,5-Dimethyl-1-pyrrolyl)-7-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 197029501-(Methoxycarbonylmethyl)-7-(2,5-dimethyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.2 g (6.8 mmol) of 6-(2,5-dimethyl-1-pyrrolyl)-7-trifluoromethyl-2,3(1H,4H)-quinoxalinedione (Example 11) were dissolved in 25 ml of anhydrous dimethylformamide under nitrogen and 0.245 g (8.2 mmol) of 80% sodium hydride was added a little at a time. The mixture was stirred at room temperature for 1 hour and then the solution was cooled to -25° C., and 1.4 g (8.9 mmol) of ethyl bromoacetate dissolved in 3 ml of dimethylformamide were added dropwise. The mixture was stirred for 90 minutes and then poured onto ice, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and evaporated in a rotary evaporator. The residue was purified by chromatography on silica gel (mobile phase: n-heptane/ethyl acetate=2/1), resulting in 0.8 g (30%) of the product.

Workup

  1. temperaturethe solution was cooled to -25° C.
  2. additionwere added dropwise
  3. stirringThe mixture was stirred for 90 minutes
  4. additionpoured onto ice
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was dried
  7. customevaporated in a rotary evaporator
  8. customThe residue was purified by chromatography on silica gel (mobile phase: n-heptane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-5bd9e7c0f06c42bc9e2f8c255fc13c32
Source dataset
uspto-grants-1998_12
Patent number
US05852017

Reaction notes

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