HCID 86602491, compound → HCID 66961235, compound

HRID 2247600Notes

Reaction equation

HRID 2247600 reaction equation
[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][C:14]3=[N:17]O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[C].[Pd]>[N:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH:14]3[NH2:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86602491HCID 86602491, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66961235HCID 66961235, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of crude 7-morpholin-4-yl-3,4-dihydro-2H-naphthalen-1-one oxime (384 mg) and 10% palladium-carbon (water content: 48%, 350 mg) in ethanol (10 mL) was stirred in a hydrogen atmosphere (0.4 Mpa) at room temperature for 8 hours. The reaction solution was filtered on a celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 110 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. filtrationThe reaction solution was filtered on a celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-a8c63b315c6d4c2c8a7aac4f6dd26703
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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