Sodium Acetate → 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

HRID 398788Notes

Reaction equation

HRID 398788 reaction equation
[Cl:1][C:2]1(Cl)[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][C:12]3[C:17]([C:5]=2[CH2:4][CH2:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C([O-])(=O)C.[Na+].O.[PH2]([O-])=O.[Na+]>C(O)(=O)C.[Pd]>[Cl:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][C:12]3[C:17]([C:5]=2[CH2:4][CH2:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 18968914HCID 18968914, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 189689123-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepineYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
56 °C

Procedure

A solution of 3,3-dichloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho- [2,1-b]azepine (28.0 g, 100 mmol) in glacial acetic acid (250 ml) was placed under an atmosphere of nitrogen. Sodium acetate (22.6 g, 275 mmol), sodium hypophosphite hydrate (24.6 g, 280 mmol) and palladium on carbon (10%, 1.5 g) were added. The reaction mixture was stirred at 56° C. for 20 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and then filtered. The solid was boiled with THF (3×700 ml) and filtered while still warm. The combined THF phases were evaporated in vacuo to give 19.1 g of 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho-[2,1-b]azepine.

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. filtrationfiltered
  4. temperaturewhile still warm
  5. customThe combined THF phases were evaporated in vacuo

Sources & evidence

ORD record
ord-97e51a38bf524c7e9ef76e2f9c411718
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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