HCID 13603773, compound → HCID 13603774, compound

HRID 653420Notes

Reaction equation

HRID 653420 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C:12](OC)=[O:13])[C:6]=1[N+:16]([O-])=O.[H][H]>O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[NH:16][C:12](=[O:13])[CH2:11]2

Participants

6

Reactant 2

HCID 13603773HCID 13603773, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13603774HCID 13603774, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-nitro-1,3-benzenediacetic acid dimethyl ester (5.98 g, 0.022 mole) in tetrahydrofuran and methanol (2:1, 100 ml) is treated with hydrogen gas in the presence of 20% Pd/C for 18 hours. The mixture is filtered and concentrated at reduced pressure to yield 2,3-dihydro-2-oxo-1H-indole-7-acetic acid methyl ester. Final purification is accomplished using flash chromatography on silica (elution with 1:19 methanol:dichloromethane) and results in pure 2,3-dihydro-2-oxo-1H-indole-7-acetic acid methyl ester, mp 156°-157° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-9e55c156ea9944019f9619a5942146f6
Source dataset
uspto-grants-1987_06
Patent number
US04677112

Reaction notes

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