Ethanol → 3-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

HRID 647853Notes

Reaction equation

HRID 647853 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:15])=[N+]=[N-].C(O)C.CCOCC>[Ni].O>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 3283Diethyl EtherHCID 109325203-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 962WaterSolvent

Procedure

To a solution of 3-azido-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (see Example 1) (27 g) in 2B ethanol (3500 ml) stirring at room temperature under an atmosphere of nitrogen, a suspension of Raney nickel in water (50 ml, washed with 10 volumes of ethanol) was added. The mixture was stirred at room temperature for 2 hours when an additional 30 ml of Raney nickel suspension was added. After stirring for an additional 30 minutes, the catalyst was filtered off and the solvent removed under reduced pressure to give an oil which solidified on addition of ether to give 3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, melting at 161°-162°.

Workup

  1. additionwas added
  2. additionwas added
  3. filtrationthe catalyst was filtered off
  4. customthe solvent removed under reduced pressure
  5. customto give an oil which

Sources & evidence

ORD record
ord-1f3f615353694656afcccf9f0bb1c8c2
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

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