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 2290211Notes

Reaction equation

HRID 2290211 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 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/charcoal in 200 ml of glacial acetic acid is hydrogenated at 50° C. under a hydrogen pressure of 5 bar. After the catalyst has been filtered off, the solvent is concentrated by evaporation 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 sulfate, evaporated, 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
  3. concentrationthe solvent is concentrated by evaporation in vacuo
  4. extractionAfter extraction with sodium bicarbonate solution
  5. washwashing with water
  6. dry with materialthe product is dried over magnesium sulfate
  7. customevaporated
  8. custompurified over silica gel with methylene chloride

Sources & evidence

ORD record
ord-fd347a673b21479093f60cfda6cfdf30
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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