5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one → 5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one

HRID 2352779Notes

Reaction equation

HRID 2352779 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 687018775-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 686983145-(4-Amino-benzyl)-1,3-dihydro-indol-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(4-Nitro-benzyl)-1,3-dihydro-indol-2-one (0.524 g, 1.94 mmols) was suspended in 35 ml of MeOH. 5% Pd/C (50 mg) was added to the flask which then was placed on a PARR apparatus. The flask was evacuated then charged with H2(g) (55 psi). This evacuation/H2(g) fill procedure was repeated 3 times (to degas the reaction mixture). The reaction vessel charged with H2(g) (55 psi) was shaken on the PARR apparatus for 2.5 hours after which the contents were filtered through celite. The organic solution was then concentrated in vacuo affording 5-(4-Amino-benzyl)-1,3-dihydro-indol-2-one at 58% yield (0.267 g, 1.12 mmol).

Workup

  1. customThe flask was evacuated
  2. additionthen charged with H2(g) (55 psi)
  3. customto degas the reaction mixture)
  4. additionThe reaction vessel charged with H2(g) (55 psi)
  5. filtrationwere filtered through celite
  6. concentrationThe organic solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-cb9e5286896c4fb5b91ec277f5e865ba
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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