HCID 69074084, compound → HCID 69065503, compound

HRID 2374482Notes

Reaction equation

HRID 2374482 reaction equation
[CH2:1]([C:3]1([CH2:19][CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[N:5]([CH:15]([CH3:17])[CH3:16])[C:4]1=[O:18])[CH3:2]>CO.O1CCCC1.[Pd]>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH:15]([CH3:16])[CH3:17])[C:4](=[O:18])[C:3]2([CH2:19][CH3:20])[CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 69074084HCID 69074084, compound

Product 1

HCID 69065503HCID 69065503, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3,3-diethyl-1-isopropyl-5-nitro-1,3-dihydro-indol-2-one (12.6 g, 45.60 mmol) in methanol/tetrahydrofuran (THF) (1:1, 80 ml) palladium on charcoal (10%, 1.2 g) was added and the mixture hydrogenated at room temperature for 4 h. After filtration of the catalyst the solvent was evaporated and the residue triturated with iso-hexane to yield 9.7 g 5-amino-3,3-diethyl-1-isopropyl-1,3-dihydro-indol-2-one (39.37 mmol, 86%).

Workup

  1. filtrationAfter filtration of the catalyst the solvent
  2. customwas evaporated
  3. customthe residue triturated with iso-hexane

Sources & evidence

ORD record
ord-5f63f20cea1a47bfac90d42151152e1c
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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