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

HRID 1456632Notes

Reaction equation

HRID 1456632 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-]>CO.C(O)C.[Pd]>[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

4

Reactant 1

HCID 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 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

To a suspension of 10.0 g (49.4 mmol) of 3-azido-2,3,4,5-tetrahydro-1H-[1]-benzazapin-2-one (Example 3 above) in 100 mL of methanol/ethanol (1:1) was added 1 g of 10% palladium on charcoal and the flask was purged with nitrogen and charged with 55 psig hydrogen. The mixture was shaken for 5 h, filtered through celite and concentrated. The residue was recrystallized from MEOH to give 6.77 g (78%) in two crops. 1H NMR (300 MHz, CDCl3) d 8.38 (1H, bs), 7.3-7.1 (3H, m), 6.98 (1H, d, J=8 Hz), 3.42 (1H, dd, J=11, 7 Hz), 2.90 (1H, m), 2.70-2.40 (2H, m), 1.89 (1H, m), 1.78 (bs, 2H).

Workup

  1. customthe flask was purged with nitrogen
  2. additioncharged with 55 psig hydrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customThe residue was recrystallized from MEOH
  6. customto give 6.77 g (78%) in two crops

Sources & evidence

ORD record
ord-b14ad014430f47b1942513e31bab5ec2
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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