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

HRID 731934Notes

Reaction equation

HRID 731934 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-94f31b215aa44b4b845ad39642e5dac5
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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