N-allyl-5-azaisatin → 1H-Pyrrolo[3,2-c]pyridine-2,3-dione

HRID 215792Notes

Reaction equation

HRID 215792 reaction equation
C([N:4]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[C:5]1=[O:6])C=C>C1(C)C=CC=CC=1>[NH:4]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[C:5]1=[O:6]

Participants

3

Reactant 1

HCID 19390720N-allyl-5-azaisatin

Product 1

HCID 107019651H-Pyrrolo[3,2-c]pyridine-2,3-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-allyl-5-azaisatin (5.3 mmol), (Ph3P)3RhCl (0.5 mmol) in aqueous toluene is stirred under a nitrogen atmosphere at room temperature overnight. The organic layer is dried (MgSO4) and the solvent is evaporated. The residue is stirred in 1N HCl/MeOH for 15 min after which time the methanol is evaporated and the pH of the water is adjusted to 7. A precipitate is formed and purified by silica gel chromatography (1% MeOH:CHCl3) to obtain the title compound.

Workup

  1. dry with materialThe organic layer is dried (MgSO4)
  2. customthe solvent is evaporated
  3. customis evaporated
  4. customA precipitate is formed
  5. custompurified by silica gel chromatography (1% MeOH:CHCl3)

Sources & evidence

ORD record
ord-1b821936825e4bb88acc22bd5f8f91ee
Source dataset
uspto-grants-2012_06
Patent number
US08193185B2

Reaction notes

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