1,4-Dioxane → HCID 22449420, compound

HRID 2257841Notes

Reaction equation

HRID 2257841 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH2:5][CH2:6][C:7]2=[O:15].O1CCOCC1>[Pd].C(O)C>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[C:7](=[O:15])[CH2:6][CH2:5][CH:4]2[N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 22449417HCID 22449417, compound

Product 1

HCID 22449420HCID 22449420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 320 mg of the compound prepared in (1) above were added 9 ml of dioxane and 15 ml of ethanol. The mixture was catalytically hydrogenated with 200 mg of 10% palladium-on-carbon. The catalyst was removed by filtration, the filtrate was concentrated, and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (2:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 176 mg of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto obtain fractions
  4. additioncontaining the target compound
  5. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-823d6162ec0846d887394646588fcc78
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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