Sodium Acetate → 3-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 647840Notes

Reaction equation

HRID 647840 reaction equation
[Cl:1][C:2]1(Cl)[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].C([O-])(=O)C.[Na+].[H][H]>C(O)(=O)C.[Pd]>[Cl:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 7311798AN-651/40768841HCID 178418361HCID 178418361, compound

Product 1

HCID 132434963-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3,3-dichloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (20 g, 0.174 mol) and anhydrous sodium acetate (15.4 g, 0.188 mol) in glacial acetic acid (920 ml) was hydrogenated at atmospheric pressure using 5% Pd-C (1.72 g) as catalyst until the uptake of hydrogen ceased. The catalyst was filtered off and the acetic acid evaporated under reduced pressure. The residue was equilibrated between 10% (NaHCO3 (900 ml) and dichloromethane (300 ml). The aqueous layer (pH 8) was further extracted with dichloromethane (3×300 ml) and the combined organic solutions were dried over anhydrous sodium sulfate and evaporated to give 3-chloro-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 163°-167°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe acetic acid evaporated under reduced pressure
  3. extractionThe aqueous layer (pH 8) was further extracted with dichloromethane (3×300 ml)
  4. dry with materialthe combined organic solutions were dried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9df9e21fd25948dbbc21758f4a183665
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

Loading…