7-Nitrooxindole → 7-aminoindolin-2-one

HRID 1844103Notes

Reaction equation

HRID 1844103 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2

Participants

5

Reactant 2

HCID 64248387-NitrooxindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 64233127-aminoindolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-nitroindoline-2-one in methanol (1.0 gm/60 mL), added Pd/C (300 mg, 30 wt %). H2 gas maintained with pressure using hydrogen gas balloon, solution stirred for 4 hours at RT. The catalyst was removed by filtration over celite. The filtrate was concentrated in vacuo to give crude product, which was washed with diethyl ether to afford compound 7-aminoindolin-2-one; YD: 76.77%; mp: 248-251° C.; Rf: 0.6 (CHCl3:MeOH: 9.0:1.0). 1H NMR (DMSO-d6) 200 MHz, δ: 3.382 (s, 2H), 4.794 (s, 2H), 6.453-6.498 (m, 2H), 6.673 (t, J=8.0 Hz, 1H), 9.906 (s, 1H). MS (ESI): m/z 146.8 [M−H]−.

Workup

  1. temperatureH2 gas maintained with pressure
  2. customThe catalyst was removed by filtration over celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give crude product, which
  5. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-e8b9700d77af4eed8d017d91d79917ea
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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