HCID 18968914, compound → 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine

HRID 398784Notes

Reaction equation

HRID 398784 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.O.O.O.C([O-])(=O)C.[Na+].[H][H]>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 18968914HCID 18968914, compoundHCID 23665404Sodium Acetate TrihydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 189689123-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepineYield 31.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3,3-dichloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine (6.2 g, 22 mmol) in glacial acetic acid (200 ml) was placed under an atmosphere of nitrogen. Sodium acetate trihydrate (3.8 g, 28 mmol) was added. After 5 minutes palladium on carbon (10%, 0.6 g) was added and the reaction mixture was hydrogenated at atmospheric pressure and room temperature using 450 ml of hydrogen gas. The reaction mixture was filtered through Celite and the solvent was evaporated in vacuo. After reevaporation with toluene (250 ml), the residue was suspended in water (100 ml), stirred for 5 minutes and the solid was isolated by filtration and dried in vacuo to afford 1.7 g of 3-chloro-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvent was evaporated in vacuo
  4. customAfter reevaporation with toluene (250 ml)
  5. customthe solid was isolated by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d2f049a8ab8e4f7e83cc9e7b0a427137
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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