HCID 463694, compound → HCID 18372816, compound

HRID 2301332Notes

Reaction equation

HRID 2301332 reaction equation
[CH3:1][C:2]1([N:10]2[C:18](=O)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9]>C(O)(=O)C.[Zn]>[CH3:1][C:2]1([N:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9]

Participants

4

Reactant 1

HCID 463694HCID 463694, compound

Product 1

HCID 18372816HCID 18372816, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

8.2 g of 2-(3-methyl-2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione were dissolved in 470 ml of glacial acetic acid. When the solution was boiling under reflux, five 3.9 g portions of zinc dust were added at intervals of one hour. Then zinc was removed by filtration and washed with 1,4-dioxane. The filtrate was evaporated under vacuo yielding a crude product which was crystallized from ethyl alcohol. The residue obtained by evaporation of the mother liquor was purified by column chromatography (stationary phase: silica gel 60, MERCK, 40-63 mm; mobile phase: 4:1 acetone/dichloromethane). Thus 2.7 g (35%) of 3-methyl-3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione were obtained.

Workup

  1. temperatureunder reflux
  2. customThen zinc was removed by filtration
  3. washwashed with 1,4-dioxane
  4. customThe filtrate was evaporated under vacuo
  5. customyielding a crude product which
  6. customwas crystallized from ethyl alcohol
  7. customThe residue obtained by evaporation of the mother liquor
  8. customwas purified by column chromatography (stationary phase: silica gel 60, MERCK, 40-63 mm; mobile phase: 4:1 acetone/dichloromethane)

Sources & evidence

ORD record
ord-64e02ef1578747a79ccf83cac0e64379
Source dataset
uspto-grants-2002_12
Patent number
US06500845B1

Reaction notes

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