1-(Hydroxyimino)-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one → 1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 2376616Notes

Reaction equation

HRID 2376616 reaction equation
O[N:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH3:14])[C:4]1=[O:15].[H][H]>CCO.N.[Ni]>[NH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][N:5]([CH3:14])[C:4]1=[O:15]

Participants

5

Reactant 2

HCID 713578231-(Hydroxyimino)-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 210725651-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

1-Hydroxyimino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one was dissolved in EtOH/NH3 (20:1) and hydrogenated in a bomb using Raney nickel and hydrogen (500 psi/3447 kPa) at 100° C. for 10 hours. The resulting mixture was filtered and concentrated to provide an oil which was purified by silica gel chromatography to yield the title compound.

Workup

  1. customat 100° C.
  2. customfor 10 hours
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated
  5. customto provide an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-46fffd3d65494532b916a04015f91c99
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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