ethyl 2-(3-azido-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl)acetate → 3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 482777Notes

Reaction equation

HRID 482777 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[N:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]1=[O:21])=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]1=[O:21]

Participants

5

Reactant 2

HCID 13499436ethyl 2-(3-azido-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 132435253-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The reaction mixture of 3-azido-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H[1]-benzazepin-2-one (13.98 kg) and 5% palladium on carbon (1.3 kg) in anhydrous ethanol (57 liters) was hydrogenated under 3 atmospheres pressure of hydrogen for 5 hours. The pressure reactor was vented at hourly intervals to remove the accumulated nitrogen. The catalyst was removed by filtration and washed with ethyl alcohol. The solution was evaporated to dryness to give 3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one.

Workup

  1. customto remove the accumulated nitrogen
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl alcohol
  4. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-ed5eb6065a184b0e8932bb44665db567
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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