4-(2-methyl-propenyl)-1H-indole-2,3-dione → 4-isobutyl-1H-indole-2,3-dione

HRID 1263973Notes

Reaction equation

HRID 1263973 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[C:7](=[O:13])[NH:8]2>[Pd].CCOC(C)=O>[CH2:3]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[C:7](=[O:13])[NH:8]2)[CH:2]([CH3:15])[CH3:1]

Participants

4

Reactant 1

HCID 110417934-(2-methyl-propenyl)-1H-indole-2,3-dione

Product 1

HCID 219563214-isobutyl-1H-indole-2,3-dioneYield 13.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.20 g (1.0 mmol) of 4-(2-methyl-propenyl)-1H-indole-2,3-dione and 0.05 g of 10% palladium on charcoal in 25 mL of EtOAc was subjected to hydrogenation on a Parr apparatus at 46 psi for 1 h. The mixture was filtered through celite, and the filtrate was concentrated to dryness. The solid was purified by chromatography on silica gel, eluting with hexane:EtOAc (4:1), to furnish 0.027 g (13%) of 4-isobutyl-1H-indole-2,3-dione: 1H NMR (DMSO-d6): δ 0.89 (d, J=6.7 Hz, 6H), 1.86 (nonet, J=6.7 Hz, 1H), 2.72 (d, J=6.7 Hz, 1H), 6.74 (d, J=7.8 Hz, 1H), 6.86 (d, J=7.8 Hz, 1H), 7.48 (t, J=7.8 Hz, 1H), 11.03 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe solid was purified by chromatography on silica gel
  4. washeluting with hexane:EtOAc (4:1)

Sources & evidence

ORD record
ord-9bcb9a3e3d5a4f159f1aae4532bcf4d5
Source dataset
uspto-grants-2003_04
Patent number
US06541503B2

Reaction notes

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