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

HRID 1154637Notes

Reaction equation

HRID 1154637 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 201442858-methoxy-1,3-dihydro-2H-benzazepin-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

56.8 gm (0.3 mol) of 8-methoxy-1,3-dihydro-2H-benzazepin-2-one (melting point: 190-191° C.), dissolved in 600 ml of glacial acetic acid, were hydrogenated in the presence of 5 gm of 10% palladium-on-charcoal at a temperature of 80° C. under a hydrogen pressure of 5 bar for 12 hours. After filtering off the catalyst, the solvent was removed in vacuo. The residue was mixed with water and neutralized with potassium carbonate. The precipitate was suction-filtered off, washed with water and dried.

Workup

  1. customfor 12 hours
  2. filtrationAfter filtering off the catalyst
  3. customthe solvent was removed in vacuo
  4. additionThe residue was mixed with water and neutralized with potassium carbonate
  5. filtrationThe precipitate was suction-filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-184fbef93a6a4a709c2313af4b74fcc4
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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