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 1380853Notes

Reaction equation

HRID 1380853 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 hydrogen pressure (5 bar). After the catalyst has been filtered off the solvent is evaporated off in vacuo and the residue is taken up in methylene chloride. After extraction with sodium bicarbonate solution and washing with water, the mixture is dried over magnesium sulphate and concentrated and purified over silica gel with methylene chloride and then with increasing amounts of methanol (up to 10%). Yield: 12.6 g. Mp: 188°-191° C.

Workup

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

Sources & evidence

ORD record
ord-cc72d5a3ea7c42969432da70e8e9b58a
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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