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CAS No. : | 57311-36-1 | MDL No. : | MFCD03423994 |
Formula : | C10H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 177.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium borohydrid; In ethanol; toluene; | EXAMPLE 23 5-[[2-(4-Trifluoromethylphenyl)ethyl]amino]-5,6,7,8-tetrahydro-1-methyl-2(1H)-quinolinone A mixture of 2-(4-trifluoromethylphenyl)ethylamine (4.1 g), 5,6,7,8-tetrahydro-1-methyl-5oxo-2(1H)-quinolinone (3.0 g), and para-toluenesulfonic acid (256 mg) was heated in refluxing toluene (50 ml), with azeotropic removal or water, for 40 hrs. An additional 2.0 g of the amine was added and the mixture was refluxed for 36 hr. The solution was cooled, and the mixture was concentrated in vacuo. Sodium borohydride (0.6 g) was added to a solution of the residue in ethyl alcohol (50 ml), and the resulting mixture was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo, the residue was quenched with water, and the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was recrystallized from ethyl acetate/hexanes to provide, in two crops, 3.8 g (65%) of product, mp 104-106 C. ANALYSIS: Calculated for C19 H21 F3 N2 O: 65.13% C, 6.04% H, 7.99% N. Found: 65.13% C, 6.16% H, 7.97% N. |
Yield | Reaction Conditions | Operation in experiment |
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4.59 g (82%) | With sodium borohydrid In ethanol; toluene | 34 5,6,7,8-Tetrahydro-1-methyl-5-[[2-(1-napthyl)ethyl]amino]-2(1H)-quinolinone fumarate EXAMPLE 34 5,6,7,8-Tetrahydro-1-methyl-5-[[2-(1-napthyl)ethyl]amino]-2(1H)-quinolinone fumarate A mixture of 2-(1-naphthyl)ethylamine(3.7 g), 5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone (3.0 g), and para-toluenesulfonic acid (256 mg) was heated in refluxing toluene (70 ml), with azeotropic removal of water, for 24 hrs. An additional 2 g of the amine was added, and the mixture was heated for an additional 24 hrs. The solution was cooled and evaporated in vacuo. Sodium borohydride (0.60 g) was added to a solution of the residue in ethyl alcohol (70 ml), and the mixture was stirred at room temperature for 1 hr. The mixture was evaporated in vacuo, the residue was quenched with water, and the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated. The residue was purified by high performance liquid chromatography on silica gel (elution with methanol/ethyl acetate) to afford 4.59 g (82%) of product. The product was dissolved in methanol and treated with an equivalent amount of fumaric acid. The solution was evaporated in vacuo, and the residue was recrystallized from methanol. The solid was stirred in hot methanol, and the mixture was filtered to provide the analytical sample, mp 189°-191° C. ANALYSIS: Calculated for C26 H28 N2 O5: 69.33% C., 6.29% H, 6.25% N. Found: 69.38% C., 6.39% H, 6.21% N. |