Methanol → HCID 18695437, compound

HRID 1870200Notes

Reaction equation

HRID 1870200 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[C:10]([C:18]#[N:19])=[CH:9][C:8]=1[N+:20]([O-])=O)[CH3:2].[CH2:24]1[CH2:28][O:27]CC1.C[OH:30]>[C].[Pd]>[C:18]([C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][C:11]=1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])[C:28](=[O:27])[C:24](=[O:30])[NH:20]2)#[N:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 18695389HCID 18695389, compound

Product 1

HCID 18695437HCID 18695437, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A mixture of 2.00 g of N-[4-cyano-5-(1H-imidazol-1-yl)-2-nitrophenyl]glycine ethyl ester, 40 ml of THF, 8 ml of methanol and 200 mg of 10% palladium-carbon was stirred under a hydrogen gas atmosphere to reduce the nitro group. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Then, 50 ml of chloroform and 4.43 ml of triethylamine were added to the resulting residue, followed by the dropwise addition of 1.69 ml of ethyl chloroglyoxylate under ice-cooling. After stirring at room temperature for 20 hours, the reaction mixture was diluted with chloroform. The diluted mixture was washed with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Then, 60 ml of ethanol and 0.5 ml of concentrated hydrochloric acid were added to the resulting residue, followed by heating under reflux for 3 hours. After cooling, the crystals so formed were collected by filtration and dried under reduced pressure to give 1.07 g (50%) of ethyl 2-[6-cyano-2,3-dioxo-7-(1H-imidazol-1-yl)-1,2,3,4-tetrahydroquinoxalin-1-yl]acetate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThen, 50 ml of chloroform and 4.43 ml of triethylamine were added to the resulting residue
  4. additionfollowed by the dropwise addition of 1.69 ml of ethyl chloroglyoxylate under ice-
  5. temperaturecooling
  6. stirringAfter stirring at room temperature for 20 hours
  7. additionthe reaction mixture was diluted with chloroform
  8. washThe diluted mixture was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. additionThen, 60 ml of ethanol and 0.5 ml of concentrated hydrochloric acid were added to the resulting residue
  12. temperatureby heating
  13. temperatureunder reflux for 3 hours
  14. temperatureAfter cooling
  15. customthe crystals so formed
  16. filtrationwere collected by filtration
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b610111f80940b99a3894cb3911ff9e
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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