Sodium Acetate → HCID 22902034, compound

HRID 1489553Notes

Reaction equation

HRID 1489553 reaction equation
[Cl:1][C:2]1(Cl)[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:12][C:5]=2[NH:4][C:3]1=[O:19].C([O-])(=O)C.[Na+]>[C].[Pd].C(O)(=O)C>[Cl:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:12][C:5]=2[NH:4][C:3]1=[O:19]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 22902030HCID 22902030, compound

Product 1

HCID 22902034HCID 22902034, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture comprising 2.88 g (9.4 mmol) of 3,3-dichloro-8-phenyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one obtained in the Synthesis Example A-4, 0.89 g (11.89 mmol) of sodium acetate, 0.2 g of 10% palladium-carbon and 40 ml of acetic acid was catalytically hydrogenated at room temperature under 3 atm for 2 hours. After filtering off the insoluble matters, the filtrate was concentrated. Then, dichloromethane was added to the residue, followed by neutralization with a saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane phase was separated, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, a small amount of dichloromethane was added to the residue, followed by collection of crystals by filtration. Thus, 0.53 g of the title compound was obtained. The mother liquor was subjected to silica gel column chromatography. After successively eluting with hexane:ethyl acetate in a ratio ranging from 6:1 (v/v) to 3:1 (v/v) and then with dichloromethane:methanol in a ratio of 200:1 (v/v), 0.4 g of the title compound was further obtained. By combining with the one obtained above, 0.93 g of the title compound was obtained in total. Yield 36%.

Workup

  1. filtrationAfter filtering off the insoluble matters
  2. concentrationthe filtrate was concentrated
  3. additionThen, dichloromethane was added to the residue
  4. customThe dichloromethane phase was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent under reduced pressure
  8. additiona small amount of dichloromethane was added to the residue
  9. filtrationfollowed by collection of crystals by filtration

Sources & evidence

ORD record
ord-1c49aeeadf5142378fe437766daec618
Source dataset
uspto-grants-1997_10
Patent number
US05679671

Reaction notes

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