HCID 13603777, compound → HCID 13603778, compound

HRID 653423Notes

Reaction equation

HRID 653423 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[C:14]2=O)[C:5]([O:7][CH3:8])=[O:6].[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[CH2:14]2)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 13603777HCID 13603777, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13603778HCID 13603778, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 23938PalladiumSolvent

Procedure

A solution of 2,3-dihydro-2,3-dioxo-1H-indole-7-propandioic acid dimethyl ester (1.4 g, 0.0048 mole) is dissolved in acetic acid (100 ml) and in the presence of 20% Pd/C is treated with hydrogen gas at 50 psi. The solution is filtered and concentrated to yield 2,3-dihydro-2-oxo-1H-indole-7-propandioic acid dimethyl ester. This is purified by flash chromatography on silica (elution with 7:3 hexane:ethyl acetate) to give after concentration pure 2,3-dihydro-2-oxo-1H-indole-7-propandioic acid dimethyl ester, mp 161°-161.5° C.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-384f574a524a4330ab1aa81c2b7f8693
Source dataset
uspto-grants-1987_06
Patent number
US04677112

Reaction notes

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