HCID 22097096, compound → HCID 22097212, compound

HRID 861503Notes

Reaction equation

HRID 861503 reaction equation
[Cl:1][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][C:2]=1[Cl:1].[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

5

Reactant 1

HCID 22097096HCID 22097096, compound

Product 2

HCID 22097087HCID 22097087, compoundYield 8%HCID 22097212HCID 22097212, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86634690HCID 86634690, compoundSolvent

Procedure

28.9 g (89 mmol) of 6-Chloro-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione 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) to yield 2.2 g (8%) of product e1 and 18.5 g (80%) of product e2.

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-a32ba9f27d1a4d02876f34e6b9153b67
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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