HCID 22097096, compound → HCID 22097212, compound

HRID 1457558Notes

Reaction equation

HRID 1457558 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7](=[O:21])[C:6](=[O:22])[NH:5]2>O1CCCC1.CO.CN(C)C=O.[Pd]>[NH2:12][C:11]1[CH:10]=[C:9]2[C:4]([NH:5][C:6](=[O:22])[C:7](=[O:21])[N:8]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 22097096HCID 22097096, compound

Product 1

HCID 22097212HCID 22097212, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86634690HCID 86634690, compoundSolvent

Procedure

28.9 g (89 mmol) of 6-chloro-1-cyclohexyl-7-nitroquinoxaline -2,3(1H,4H)-dione were dissolved in 300 ml of tetrahydrofuran/methanol/dimethylformamide (3:3:1) and, after addition of 3 g of palladium/carbon (10%), hydrogenated. The mixture was filtered, the carbon was washed with methanolic ammonia solution, and the combined filtrates were concentrated under reduced pressure. The residue was chromatographed on silica gel with the mobile phase toluene/acetone/glacial acetic acid (10:10:1). 2.2 g (8%) of product el and 18.5 g (80%) of product e2 were obtained.

Workup

  1. filtrationThe mixture was filtered
  2. washthe carbon was washed with methanolic ammonia solution
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel with the mobile phase toluene/acetone/glacial acetic acid (10:10:1)

Sources & evidence

ORD record
ord-2cabe931f87a4b0aae7e47fa42588839
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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