1-Methyl-6-nitroindoline → 1-methyl-2,3-dihydro-1H-indol-6-amine

HRID 1939167Notes

Reaction equation

HRID 1939167 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][N:2]2[CH3:1])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 123690471-Methyl-6-nitroindoline

Product 1

HCID 123690481-methyl-2,3-dihydro-1H-indol-6-amineYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Methyl-6-nitroindoline (0.9 g) was hydrogenated at 40 psi in methanol (100 ml) containing 10% palladium on carbon (0.9 g). The reaction mixture was filtered then evaporated and the residue was purified by column chromatography on silica using hexane→50% ethyl acetate/hexane to afford the title compound (0.62 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthen evaporated
  3. customthe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-bc382abe11ab4427b78b010cda2a1519
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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