N-methanesulfonyl-6-nitroindole → N-methanesulfonyl-6-aminoindole

HRID 1106778Notes

Reaction equation

HRID 1106778 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)[CH:7]=[CH:6]1)(=[O:4])=[O:3]>CO.[Pt]=O>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 18789696N-methanesulfonyl-6-nitroindole

Product 1

HCID 18789618N-methanesulfonyl-6-aminoindole

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of N-methanesulfonyl-6-nitroindole (2.52 g, 10.5 mmol, from above) and platinum oxide (119 mg, 0.52 mmol) in 100 ml of methanol was hydrogenated in a Parr apparatus for approximately 1 hr until a constant pressure was obtained (42 psi H2 initially). The catalyst was removed by filtration (Whatman GF/F filter) and the filtrate was concentrated by rotary evaporation to give N-methanesulfonyl-6-aminoindole, an oil which solidified on standing under an argon atmosphere.

Workup

  1. customwas obtained (42 psi H2 initially)
  2. customThe catalyst was removed by filtration (Whatman GF/F filter)
  3. concentrationthe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-c28458a67c084ea3a2a1a41b8b617dbe
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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