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[ CAS No. 117052-19-4 ] {[proInfo.proName]}

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Chemical Structure| 117052-19-4
Chemical Structure| 117052-19-4
Structure of 117052-19-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 117052-19-4 ]

CAS No. :117052-19-4 MDL No. :MFCD09800420
Formula : C10H11ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 214.65 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 117052-19-4 ]

* 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.

  • Downstream synthetic route of [ 117052-19-4 ]

[ 117052-19-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 86232-28-2 ]
  • [ 117052-19-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Mg / 2.) ether, benzene, reflux, 6 h 2: 85 percent / CrO3, pyridine / CH2Cl2 / 0.25 h
  • 2
  • [ 117052-19-4 ]
  • [ 903581-03-3 ]
YieldReaction ConditionsOperation in experiment
91.7% Stage #1: 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanone With titanium(IV) isopropylate; ammonia In ethanol at 16 - 32.4℃; for 16.08 - 16.16h; Stage #2: With sodium tetrahydroborate In ethanol at 1.4 - 19℃; for 4.16h; Stage #3: With ammonia In ethanol; water at 21 - 26℃; 54 1 -(5-Chloro-2,3-dimethoxy-phenyl)-ethyl amine:; To a solution of l-(5-chloro-2,3-dimethoxy-phenyl)-ethanone (145.8 g, 0.68 mol) in NH3/EtOH (2M, 2.0 L) was added titanium isopropoxide (482 g, 1.6 mol) over 5-10 min. The temperature increased from 16 to 26 0C after half of the titanium isopropoxide had been added. After the total amount of titanium isopropoxide had been added, the temperature had increased EPO to 32.4 0C. The reaction solution was allowed to stir under nitrogen for 16 hours. It was cooled to 1.4 0C and sodium borohydride (61.7 g, 1.6 mol) was added in portions over 40 min. An exotherm was observed (temperature ranged between 5 and 19 0C). The cooling bath was removed and the reaction mixture was stirred for 3.5 hours. TLC (1 :4 heptane: acetone) showed no starting material present.0.52 L of 30 % ammonium hydroxide was diluted with water to the total volume of 2 L. The reaction mixture was added to this solution in portions (temperature increased from 21 to 26 0C). The resulting thick white slurry was separated by filtration (filtration was quite slow). Addition of ethyl acetate (~1 L) to the filtrate (~ 5 L) did not cause separation of layers. The solution was concentrated under reduced pressure to ~ 2 L volume. Ethyl acetate (1 L) and water (1 L) were added (EtOAc alone was insufficient to cause separation), the organic phase was separated, and the aq. phase was washed with 0.5 L EtOAc. The organic phases were combined, dried over sodium sulfate (~ 2 Kg) and concentrated. Upon concentration to ~ 0.5 L an oil separated from the aqueous portion. The layers were separated, the aq. layer was extracted with ~ 0.1 L EtOAc, and the oil and ethyl acetate solutions were concentrated again. Residual water was removed by chasing with 2 x 0.2 L of toluene. The oil was left under vacuum to yield 134.5 g of product (91.7 % yield, HPLC 93 % pure).
40% Stage #1: 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanone With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; for 36h; Stage #2: With hydrogenchloride In methanol; water Stage #3: With potassium hydroxide In water 25 l-(5-Chloro-2,3-dimethoxy-phenyl)-ethyl amine:; To a stirred solution of l-(5-chloro-2,3-dimethoxy-phenyl)-ethanone (3.6 g, 16.8 mmol) and ammonium acetate (12.9 g, 168 mmol) in absolute methanol (50 mL) was added sodium cyanoborohydride (0.738 g, 11.8 mmol) in one portion. The resulting solution was stirred at room temperature for 36 h. Concentrated HCl was added until pH <2. The methanol was then evaporated, and the resulting white residue was dissolved in H2O (50 mL) and washed with diethyl ether (2 x 50 mL). The aqueous phase was then basified with powdered KOH to pH >10, saturated with NaCl, and extracted with dichloromethane (4 x 10 mL). The combined dichloromethane extracts were dried over Na2SO4, filtered, and evaporated to the crude compound which was purified by silica gel column (1 %NH4OH/ 8 % methanol /dichloromethane) to afford l-(5-chloro-2,3-dimethoxy-phenyl)-ethyl amine (1.43 g, 40 %): 1H NMR (400 MHz, CDCl3): δ 6.98 (d, 1 H), 6.78 (d, 1 H), 4.39 (m, 1 H), 3.86 (s, 3 H), 3.83 (s, 3 H), 1.35 (d, 3 H).
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