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

HRID 1380858Notes

Reaction equation

HRID 1380858 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>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

4

Reactant 1

HCID 42200938-methoxy-2,3-dihydro-1H-3-benzazepin-2-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

First, 8-methoxy-1,3-dihydro-2H-3-benzazepin-2-one (56.8 g, 0.3 mol) (Mp: 190°-191° C.), dissolved in glacial acetic acid (600 ml), is hydrogenated in the presence of 10% palladium/charcoal (5 g) at 80° C. and at 5 bar for 12 hours. The catalyst is suction filtered and the acetic acid is distilled off in vacuo. The residue is mixed with water, neutralized with potassium carbonate, the precipitate obtained is suction filtered, washed with water and dried. Yield: 51.1 g. Mp: 160°-161° C.

Workup

  1. filtrationfiltered
  2. distillationthe acetic acid is distilled off in vacuo
  3. additionThe residue is mixed with water
  4. customthe precipitate obtained
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-93a1e1bb275d43bdb0c92deb9316ad96
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

Loading…