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

HRID 1340

Reaction equation

HRID 1340 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ef4bb1c6c9b74f7baca312f5b2f73584
Source dataset
uspto-grants-1998_03
Patent number
US05723606

Linked notes

Loading…