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 1154632Notes

Reaction equation

HRID 1154632 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.[H][H]>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

5

Reactant 2

HCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 178418361HCID 178418361, compound

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 21.9 gm (0.1 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one and 1.5 gm of 10% palladium-on-charcoal in 200 ml of glacial acetic acid was hydrogenated at 50° C. and at a hydrogen pressure of 5 bar. After the catalyst had been filtered off, the solvent was evaporated in vacuo, and the residue was taken up in methylene chloride. After the solution had been extracted with an aqueous sodium bicarbonate solution and washed with water, it was dried over magnesium sulfate, evaporated and purified over silica gel with methylene chloride and then with increasing amounts of methanol (up to 10%).

Workup

  1. filtrationAfter the catalyst had been filtered off
  2. customthe solvent was evaporated in vacuo
  3. extractionAfter the solution had been extracted with an aqueous sodium bicarbonate solution
  4. washwashed with water, it
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated
  7. custompurified over silica gel with methylene chloride

Sources & evidence

ORD record
ord-773dd9fed1b0405c9a4d685171c8eec5
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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