Sodium Acetate → 3-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 621433Notes

Reaction equation

HRID 621433 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.[C:15]([O-])(=[O:17])[CH3:16].[Na+]>C(OC(=O)C)(=O)C>[C:15]([N:10]1[CH2:9][CH2:8][C:7]2[CH:13]=[CH:14][C:4]([O:3][CH3:2])=[CH:5][C:6]=2[CH2:12][CH2:11]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 212429067-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

Product 1

HCID 138533493-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (4.3 g, 0.02 m) and sodium acetate (3.3 g, 0.04 m) in acetic anhydride (13 ml) was refluxed and stirred for 16 hours, concentrated in vacuo and partitioned between methylene chloride and water. The organic phase was dried with magnesium sulfate, filtered and concentrated in vacuo to give 3-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 89°-90°.

Workup

  1. temperaturewas refluxed
  2. concentrationconcentrated in vacuo
  3. custompartitioned between methylene chloride and water
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-036b219f2c4640baad59dbd5c93151c1
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

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