Ethanol → 1-(Methylsulfonyl)indolin-6-amine

HRID 2264320Notes

Reaction equation

HRID 2264320 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C(O)C>[Pd].O1CCCC1>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 702EthanolHCID 231122131-Methanesulfonyl-6-nitroindoline

Product 1

HCID 166425721-(Methylsulfonyl)indolin-6-amineYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2.00 g of 1-methylsulfonyl-6-nitroindoline and a mixed solvent of 100 ml of ethanol and 100 ml of tetrahydrofuran was added 300 mg of 10% palladium/carbon under an argon atmosphere, followed by 3 hours of stirring at room temperature under a hydrogen atmosphere. The reaction solution was filtrated through celite and the organic solvent in the filtrate was removed under reduced pressure. To the residue was added 200 ml of a mixed solution of methanol, ethyl acetate, and tetrahydrofuran. Under an argon atmosphere, 1 g of 10% palladium/carbon was added and the whole was stirred at room temperature for 3 hours under a hydrogen atmosphere. The reaction solution was filtrated through celite and the organic solvent in the filtrate was removed under reduced pressure to obtain 1.66 g of 1-methylsulfonyl-6-aminoindoline as a pale yellow solid.

Workup

  1. filtrationThe reaction solution was filtrated through celite
  2. customthe organic solvent in the filtrate was removed under reduced pressure
  3. additionTo the residue was added 200 ml of a mixed solution of methanol, ethyl acetate, and tetrahydrofuran
  4. additionUnder an argon atmosphere, 1 g of 10% palladium/carbon was added
  5. stirringthe whole was stirred at room temperature for 3 hours under a hydrogen atmosphere
  6. filtrationThe reaction solution was filtrated through celite
  7. customthe organic solvent in the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-211746b089f74f629490bf4b91119b99
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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