Dimethylformamide → 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

HRID 342302

Reaktionsgleichung

Reaktionsgleichung von HRID 342302
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.CN(C)C=O>[Ni].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:22][CH:23]=1

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 107337295H-1-Benzazepin-5-one, 1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-

Produkt 1

HCID 107078741-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A 19.2 g portion of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-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-tetrahydro-1H-1-benzazepin-5-one.

Aufarbeitung

  1. additionwas added to the resulting solution
  2. customAfter completion of the hydrogen absorption
  3. filtrationthe reaction solution was filtered
  4. concentrationconcentrated
  5. dissolutionThe thus obtained residue was dissolved in dichloromethane
  6. washwashed with a saturated sodium bicarbonate aqueous solution
  7. dry with materialThe resulting dichloromethane layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe thus obtained residue was recrystallized from methyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-d5417cc0bca1463e9be0ec527097a3b6
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856564

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