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

HRID 861480Notes

Reaction equation

HRID 861480 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-1b85d19fd9404877a42b9d91ad3daf28
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

Loading…