Acetic Acid → 8-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 648964Notes

Reaction equation

HRID 648964 reaction equation
CO[C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[CH:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1.[C:15](O)(=[O:17])C>[Pd]>[CH3:15][O:17][C:6]1[CH:13]=[CH:14][C:3]2[CH2:4][CH2:5][NH:11][C:10](=[O:12])[CH2:9][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20144285HCID 20144285, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Here, 8-methoxy-1,3-dihydro-2H-benzazepin-2-one (melting point: 190°-191° C.) (56.8 g, 0.3 mol), dissolved in glacial acetic acid (600 ml), is hydrogenated for 12 hours in the presence of 10% palladium/charcoal (5 g) at 80° C. and at 5 bar. The catalyst is removed by suction filtering 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.

Workup

  1. customThe catalyst is removed by suction
  2. filtrationfiltering
  3. distillationthe acetic acid is distilled off in vacuo
  4. additionThe residue is mixed with water
  5. customthe precipitate obtained
  6. filtrationfiltered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5c15dc6bba5f40fe9fe6dd22825eb904
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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