Réaction #2439937

Équation de réaction

MeOH CHCl3

keto-aniline

5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

→

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

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   Autreto remove any O2(g)
2. 2
   workup.ADDITIONwas then charged with H2(g) at atmospheric pressure
3. 3
   Autrehad been completely consumed
4. 4
   Autrethe reaction
5. 5
   Autreimmediately upon complete consumption of the starting material
6. 6
   FiltrationThe reaction mixture was filtered over celite
7. 7
   Concentrationthe filtrate was concentrated in vacuo
8. 8
   Autreresulting in a solid

Mode opératoire

5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one (2.0 g, 7.09 mmol) was dissolved in MeOH (600 mL). 10% Pd/C (0.20 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) at atmospheric pressure. This evacuation/H2(g) fill procedure was repeated twice. The reaction mixture was stirred for 2 h at which point the starting material had been completely consumed. 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 mixture was filtered over celite and the filtrate was concentrated in vacuo resulting in a solid that contained the desired keto-aniline product plus ˜5% of the overreduced alcohol-aniline. Flash silica gel chromatography (5% MeOH/CHCl3) of the crude solid provided pure 5-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one in 72% (0.957 g, 3.80 mmol) yield.

Source