Réaction #1436

Équation de réaction

1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one

dimethylformamide

→

1-(4-aminobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one

Solvants

methyl alcohol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added to the resulting solution
2. 2
   AutreAfter completion of the hydrogen absorption
3. 3
   Filtrationthe reaction solution was filtered
4. 4
   Concentrationconcentrated
5. 5
   workup.DISSOLUTIONThe thus obtained residue was dissolved in dichloromethane
6. 6
   Lavagewashed with a saturated sodium bicarbonate aqueous solution
7. 7
   SéchageThe resulting dichloromethane layer was dried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated under a reduced pressure
9. 9
   AutreThe thus obtained residue was recrystallized from methyl alcohol

Mode opératoire

A 19.2 g portion of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one was dissolved in a mixed solvent consisting of 200 ml of dimethylformamide and 100 ml of methyl alcohol, and 3 ml of Raney nickel was added to the resulting solution to carry out hydrogenation at normal pressure. After completion of the hydrogen absorption, the reaction solution was filtered and concentrated. The thus obtained residue was dissolved in dichloromethane and then washed with a saturated sodium bicarbonate aqueous solution. The resulting dichloromethane layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The thus obtained residue was recrystallized from methyl alcohol to obtain 15.5 g of 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one.

Source