1,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one → 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

HRID 648955Notes

Reaction equation

HRID 648955 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

Product 1

HCID 114017697,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one (21.9 g, 0.1 mol) and 10% palladium/charcoal (1.5 g) in glacial acetic acid (200 ml) is hydrogenated at 50° C. under a hydrogen pressure of 5 bar. After the catalyst has been filtered off the solvent is evaporated in vacuo and the residue is taken up in methylene chloride. After extraction with sodium bicarbonate solution and washing with water, the product is dried over magnesium sulphate, concentrated by evaporation and purified over silica gel with methylene chloride and then with increasing amounts of methanol (up to 10%).

Workup

  1. customis hydrogenated at 50° C. under a hydrogen
  2. filtrationAfter the catalyst has been filtered off the solvent
  3. customis evaporated in vacuo
  4. extractionAfter extraction with sodium bicarbonate solution
  5. washwashing with water
  6. dry with materialthe product is dried over magnesium sulphate
  7. concentrationconcentrated by evaporation
  8. custompurified over silica gel with methylene chloride

Sources & evidence

ORD record
ord-04c6be61b72646a7b422c1fdb6bb4583
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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