5-Isopropylamino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one → 6-Amino-5-isopropylamino-3,3-dimethyl-1-pentyl-1,3-dihydro-indol-2-one

HRID 2235459Notes

Reaction equation

HRID 2235459 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9](=[O:22])[C:8]2([CH3:24])[CH3:23])([CH3:3])[CH3:2]>CN(C)C=O.[Pd]>[NH2:14][C:13]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:24])([CH3:23])[C:9](=[O:22])[N:10]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:6][C:5]=1[NH:4][CH:1]([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 674274925-Isopropylamino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one

Product 1

HCID 674272526-Amino-5-isopropylamino-3,3-dimethyl-1-pentyl-1,3-dihydro-indol-2-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Isopropylamino-3,3-dimethyl-6-nitro-1-pentyl-1,3-dihydro-indol-2-one (200 mg) is dissolved in N,N-dimethylformamide (10 ml) and hydrogenated at RT at 3 bar for 12 h using Pd/C (10%; 0.1 g) as catalyst. After completion of the reaction the mixture is filtered and evaporated to give the compound (180 mg).

Workup

  1. customAfter completion of the reaction the mixture
  2. filtrationis filtered
  3. customevaporated

Sources & evidence

ORD record
ord-683e9cf6a17f4091985f8279a337732a
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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