HCID 59129756, compound → HCID 11469773, compound

HRID 2424334Notes

Reaction equation

HRID 2424334 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([NH2:14])=[O:13])[C:6](=[O:15])[C:5]12SCCS1>[Ni].C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([NH2:14])=[O:13])[C:6](=[O:15])[CH2:5]2

Participants

4

Reactant 1

HCID 59129756HCID 59129756, compound

Product 1

HCID 11469773HCID 11469773, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

The Raney Nickel was prepared as an aqueous slurry after removing four fifth of water of the commercial solution. Aqueous Raney nickel (10 ml) was added to a solution of compound 15 (4.06 g, 13.8 mmol) in 40 ml of distilled THF and the mixture was further vigourously stirred at room temperature. When no starting material was detected by thin layer chromatography, the mixture was diluted with THF and filtered through a Celite pad. After removal of the solvent, the crude material was purified by silica gel chromatography (CH2Cl2/MeOH 95/5 then 90/10), and the solvent was evaporated to yield the 2-(5-methyl-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 24 as a white solid.

Workup

  1. customafter removing four fifth of water of the commercial solution
  2. filtrationfiltered through a Celite pad
  3. customAfter removal of the solvent
  4. customthe crude material was purified by silica gel chromatography (CH2Cl2/MeOH 95/5
  5. custom90/10), and the solvent was evaporated

Sources & evidence

ORD record
ord-6a09bedc48ec49258dc3d9c6e0b9b416
Source dataset
uspto-grants-2011_06
Patent number
US07964593B2

Reaction notes

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