8-methoxy-2,3-dihydro-1H-3-benzazepin-2-one → 8-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 621431Notes

Reaction equation

HRID 621431 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][NH:10][C:9](=[O:13])[CH2:8][C:7]=2[CH:14]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C:9](=[O:13])[CH2:8][C:7]=2[CH:14]=1

Participants

5

Reactant 2

HCID 42200938-methoxy-2,3-dihydro-1H-3-benzazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 135206858-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2,3-dihydro-8-methoxy-2-oxo-1H-3-benzazepine (12 g, 0.063 m) and 10% palladium-on-carbon (1.2 g) in acetic acid (200 ml) was shaken in an atmosphere of hydrogen (60 psi), degassed, filtered and concentrated in vacuo. The residue was dissolved in methylene chloride, washed with water, dried with magnesium sulfate and concentrated in vacuo. The residue was triturated with ether and filtered to give 8-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. customdegassed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-73a3c047791e449c9f3a6b4e7cdf16a0
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

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