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[ CAS No. 73257-49-5 ]

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Chemical Structure| 73257-49-5
Chemical Structure| 73257-49-5
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CAS No. :73257-49-5 MDL No. :MFCD00619418
Formula : C17H18ClNO4 Boiling Point : 448.4±45.0°C at 760 mmHg
Linear Structure Formula :C17H18NO4Cl InChI Key :-
M.W :335.78 g/mol Pubchem ID :726133
Synonyms :

Safety of [ 73257-49-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73257-49-5 ]

  • Upstream synthesis route of [ 73257-49-5 ]
  • Downstream synthetic route of [ 73257-49-5 ]

[ 73257-49-5 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
91% With ammonium hydroxide In ethanol at 110℃; Flow reactor General procedure: Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (4a). EtOH solution (3 mL) ofbenzaldehyde (0.67 M) mixed with ethyl acetoacetate (1.34 M) and the 25percent aqueous NH3 (3 mL) wererespectively transferred into gas-tight syringe 1 and syringe 2. The syringes were placed in a LongerLSP02-1B syringe pump which was set to deliver the reactants into the mixer at identical flow rate of 6.7μL/min. The reaction mixture was then allowed to flow through a stainless steel tube reactor which wasdipped in a 110 C oil bath. The output mixture was collected in a cooled sample vial. After reactioncompletion, rinsed the reactor with ethanol to collect all of the reactant solution and then concentratedunder vacuum. The residue was subjected to silica gel column chromatography with Pet-EA (5:1) aseluent to give 4a (612mg, 93percent yield).
Reference: [1] Heterocycles, 2016, vol. 93, # 2, p. 755 - 761
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YieldReaction ConditionsOperation in experiment
84% With ammonium acetate In neat (no solvent) at 55℃; for 3 h; Green chemistry General procedure: Polyhydroquinolines and DihydropyridinesA mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue
Reference: [1] Synlett, 2014, vol. 25, # 19, p. 2753 - 2756
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YieldReaction ConditionsOperation in experiment
96% With iron supported on copper/Zeolite Socony Mobil-5 nanocatalyst In water at 20℃; Sonication General procedure: In a typical experiment, aromatic aldehyde (1 mmol), bketoester(2 mmol), ammonium acetate (1 mmol), and Fe-Cu/ZSM-5 (3 wtpercent) in 2 ml water were introduced in a 20-mL heavy-walled pear-shaped two-necked flask with nonstandard-tapered outer joint. The flask was attached to a12-mm tip diameter probe, and the reaction mixture was sonicated at ambient temperature at 20 percent power of the processor. After completion of the reaction (monitored byTLC, within 5–8 min), the solid product was filtered,washed with water and ethanol, dried, and recrystallized from ethanol. The supported reagent was washed thrice with water and ethanol and dried under vacuum before reuse.
Reference: [1] Journal of the Iranian Chemical Society, 2016, vol. 13, # 2, p. 267 - 277
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YieldReaction ConditionsOperation in experiment
95% at 80℃; for 0.3 h; General procedure: A mixture of the alkyl or aryl aldehyde (1 mmol), -dicarbonyl(2 mmol) and ammonium acetate (1.5 mmol) in the presence ofFe3O4NPs (0.024 g, equal to 10 molpercent) was heated at 80C, withstirring. The progress of the reaction was monitored by TLC (elu-ent: EtOAc:n-hexane). After completion of the reaction, the mixturewas cooled to room temperature and then ethanol was added tothe resulting mixture and separated Fe3O4NPs by a normal mag-net. After evaporation of solvent, the solid product was filtered andrecrystallized from ethanol to give the pure products in 72–95percentyields based on the starting aldehyde.
95% With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10 h; In a 100 mL single-necked flask, 0.01 molpercent of Lewis acid-base bifunctional catalyst I was added (where Rf = CF3R1,R2, R3, R4, R5, R6 = F), 0.1 mol of p-chlorobenzaldehyde (R7 = 4-Cl-Ph), 0.1 mol of methyl acetoacetate (R8 = Me;Me), 0.1 mol of ammonium acetate, 10 mL of toluene, and the reaction was stirred at 100 ° C for 10 hours. TLC followed the reaction to complete the reaction. anti-The yield of the product II (R7 = 4-Cl-Ph; R8 = Me; R9 = Me) was 95percent; the catalyst system was reused 10 timesAfter its catalytic performance did not decline
94% for 2.25 h; Heating; Green chemistry General procedure: A mixture of aldehyde 1 (1 mmol), 1,3-dicarbonyl compound 2 (2 mmol), and nitrogen source 3 (3 mmol) were mixed and heated in the presence of a low-melting sugar mixture.The progress of the reaction was monitored by thin-layer chromatography (TLC) using n-hexane–ethyl acetate (7:3) as the solvent system. The Rf values of the product spots ranged from 0.5 to 0.6. After completion of the reaction, water was added to the reaction mixture to obtain the solid product as a precipitate. In cases where the product was obtained as a melt, several washings with water followed by bicarbonate solution gave crystalline products. The solids were filtered and washed with cold water. In most of the cases, the product obtained was pure, and when impure, the product was recrystallized from hot ethanol. Further two products were obtained as oils (Table 5, entries 4w and 4x). These products were extracted with ethyl acetate and dried over anhydrous Na2SO4. Evaporation of the solvent gave the pure product as an oil.
91% at 100℃; for 0.25 h; Green chemistry General procedure: To a glassy reactor equipped with a magnetic stir bar, amixture of aromatic aldehyde (1.0 mmol), β-keto ester(2 mmol), ammonium acetate (1.5 mmol) and n-Fe3O4(at)ZrO2/HPW (0.003 g, 15 mol percent) was added. The reactorwas put in an oil bath with the temperature of 100 °C andthe reaction was carried out under solvent-free condition.The progress of the reaction was monitored using TLCplates. When the reaction was completed, the mixture wasallowed to cool to room temperature. Afterwards, the mixturewas triturated with 5mL ethyl acetate and the catalystwas separated by the help of an external magnet. Then thesolvent was evaporated and the crude product was recrystallizedfrom EtOH/H2O to offer the pure product.
90% With uranyl nitrate hexahydrate; ammonium acetate In ethanol at 20℃; for 0.416667 h; Sonication General procedure: To a solution of aldehyde (1.0 mmol), ethyl/methyl acetoacetate/acetylacetone (2.0 mmol) and ammonium acetate (1.0 mmol) in ethanol (3 mL), uranyl nitrate (10 molpercent) was added and the resultant reaction mixture was sonicated at room temperature for the required time (Table 1). The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured into crushed ice. The obtained solid was filtered, washed thoroughly with water, dried, and purified by recrystallisation in ethanol.
84% at 55℃; for 3 h; Green chemistry General procedure: A mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue.
74% With C21H38N(1+)*Mo11O40PV(4-)*3H(1+); ammonium acetate In ethanol at 78℃; for 8 h; Green chemistry General procedure: The reaction was performed in a round bottom flask, whichwas equipped with a condenser and immersed in an oil bath. A mixture of methylacetoacetate (232 mg, 2 mmol), 2-nitrobenzaldehyde(151 mg, 1 mmol), ammonium acetate(100 mg, 1.3 mmol), and the selected catalyst (30 mg,1.5 percent mmol), in ethanol (8 mL) was thoroughly mixed andthen heated at 78 °C for 8 h. (to the end point of the reaction,checked by TLC). On cooling, the reaction mixture wasfiltered to separate the catalyst, the ethanol was evaporated,and the crude 1,4-dihydropyidine obtained was dried undervacuum (25 °C). The solid catalyst was washed with hexane(2 x 1 mL) and then, H2O (2 x 1 mL). The crude productwas recrystallized to give the pure 1,4-dihydropyridine.

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Reference: [1] Journal of Materials Chemistry A, 2013, vol. 1, # 37, p. 11210 - 11220
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8083 - 8086
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Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 5, p. 745 - 747
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Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 652 - 653
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Reference: [1] Synthesis, 2010, # 23, p. 4057 - 4060
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