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

HRID 640841Notes

Reaction equation

HRID 640841 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-121f960d1a54461ca67d2e0caf98e5ba
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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