Sulfuric Acid → HCID 53936879, compound

HRID 845494Notes

Reaction equation

HRID 845494 reaction equation
[CH2:1]([CH:5]1[CH2:13][CH2:12][CH:11]2[CH:7]([C:8](=O)[C:9](=[O:14])[NH:10]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].[H][H].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd].[Rh]>[CH2:1]([CH:5]1[CH2:13][CH2:12][CH:11]2[CH:7]([CH2:8][C:9](=[O:14])[NH:10]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 56994825HCID 56994825, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53936879HCID 53936879, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

For example, a solution of 5-n-butyl-octahydro-2,3-dioxo-1H-indole (III) (43.6 g, 0.214 mole) in acetic acid (250 ml) is treated with hydrogen gas in the presence of 20% Pd/C (2 g). Another 1 g of 20% Pd/C is added and concentrated sulfuric acid (1 ml) is added and the hydrogenation is continued. Ten percent Rh/C (2 g) is added and hydrogenation is continued. The suspension is filtered and sodium acetate (4.9 g, 0.06 mole) is added and the mixture is concentrated at reduced pressure The residue is recrystallized from cyclohexane with the use of activated carbon to yield pure 5-n-butyloctahydro-2-oxo-1H-indole (V) with a mp 109°-111° C.

Workup

  1. filtrationThe suspension is filtered
  2. concentrationthe mixture is concentrated at reduced pressure The residue
  3. customis recrystallized from cyclohexane with the use of activated carbon

Sources & evidence

ORD record
ord-f17a93c4863749e7a6f3b00ddea050a1
Source dataset
uspto-grants-1988_07
Patent number
US04758585

Reaction notes

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