Nitrosobenzene → 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

HRID 640828

Reaction equation

HRID 640828 reaction equation
[N+]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13]3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.O=[N:23]C1C=CC=CC=1>CO.[Pd]>[NH2:23][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:4]=1)[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13]2)=[O:9]

Participants

5

Reactant 2

HCID 11473NitrosobenzeneHCID 687007145-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Product 1

HCID 644240015-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one (1.51 g, 5.28 mmol) was dissolved in MeOH (600 mL). 10% Pd/C (0.150 g) was added to the flask and then placed under vacuum to remove any O2(g). The reaction mixture was kept under reduced pressure for 5 min and was then charged with H2(g). This evacuation/H2(g) fill procedure was repeated twice. The reaction mixture changed from a cloudy grayish/black color to a translucent dark green/black color, signifying complete consumption of the starting material. As the desired ketone product was prone to over-reduction to the alcohol, stopping the reaction immediately upon complete consumption of the starting material limited the amount over-reduction that occurred. The reaction was allowed to run for 0.75-1.0 hours after which, the reaction mixture was filtered over celite and concentrated in vacuo resulting in a yellowish solid that contained the desired keto-aniline product plus ˜5% of the overreduced alcohol-aniline. The crude solid was purified by triturating with MeOH. The desired keto-aniline product, 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one was soluble in MeOH and was filtered away from the insoluble over reduced alcohol by-product. In vacuo concentration of the methanolic filtrate provided pure 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one in 72% (0.957 g, 3.80 mmol) yield.

Workup

  1. customto remove any O2(g)
  2. additionwas then charged with H2(g)
  3. customconsumption of the starting material
  4. customthe reaction
  5. customimmediately upon complete consumption of the starting material
  6. waitto run for 0.75-1.0 hours
  7. filtrationafter which, the reaction mixture was filtered over celite and
  8. concentrationconcentrated in vacuo
  9. customresulting in a yellowish solid
  10. customThe crude solid was purified
  11. customby triturating with MeOH
  12. filtrationwas filtered away from the insoluble over reduced alcohol by-product

Sources & evidence

ORD record
ord-71f4d4aacc3a4936a5985335c6851d1f
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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