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Product Citations

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Christian N. Lotz ; Alina Krollenbrock ; Lea Imhof , et al. DOI:

Abstract: Schistosomiasis caused by Schistosoma spp. is a disease that causes a considerable health burden to millions of people worldwide. The limited availability of effective drugs on the market and the increased risk of resistance development due to extensive usage, highlight the urgent need for new antischistosomal drugs. Recent studies have shown that robenidine derivatives, containing an aminoguanidine core, exhibit promising activities against Plasmodium falciparum, motivating further investigation into their efficacy against Schistosoma mansoni, due to their similar habitat and the resulting related cellular mechanisms like the heme detoxification pathway. The conducted phenotypic screening of robenidine and 80 derivatives against newly transformed schistosomula and adult Schistosoma mansoni yielded 11 candidates with low EC50 values for newly transformed schistosomula (1.12–4.63 μM) and adults (2.78–9.47 μM). The structure-activity relationship revealed that electron-withdrawing groups at the phenyl moiety, as well as the presence of methyl groups adjacent to the guanidine moiety, enhanced the activity of derivatives against both stages of Schistosoma mansoni. The two compounds 2,2′-Bis[(3-cyano-4-fluorophenyl)methylene] carbonimidic Dihydrazide Hydrochloride (1) and 2,2′-Bis[(4-difluoromethoxyphenyl) ethylidene] carbonimidic Dihydrazide Hydrochloride (19), were selected for an in vivo study in Schistosoma mansoni-infected mice based on their potency, cytotoxicity, pharmacokinetic-, and physicochemical properties, but failed to reduce the worm burden significantly (worm burden reduction <20%). Thus, robenidine derivatives require further refinements to obtain higher antischistosomal specificity and in vivo activity.

Keywords: Robenidine derivative ; Aminoguanidine ; Schistosoma mansoni ; Drug discovery ; Structure-activity relationship

Purchased from AmBeed: ; ; ; ; ; ; ;

Jan Nowak ; Michał Tryniszewski ; Michał Barbasiewicz DOI:

Abstract: Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

Keywords: olefination ; carbonyl compounds ; reaction mechanism ; lactones ; malonates ; Knoevenagel ; Doebner reaction

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du Preez, Charne ; Legoabe, Lesetja J. ; Jordaan, Audrey , et al. DOI: PubMed ID:

Abstract: Curcumin is a natural product that has been reported to exhibit myriad pharmacol. properties, one of which is antitubercular activity. It demonstrates antitubercular activity by directly inhibiting Mycobacterium tuberculosis (M.tb) and also enhances immune responses that ultimately lead to the elimination of M.tb by macrophages. This natural product is, however, unstable, and several analogs, noticeably monocarbonyl analogs, have been synthesized to overcome this challenge. Curcumin and its monocarbonyl analogs reported so far exhibit moderate antitubercular activity in the range of 7 to 16 μM. Herein, we report a straightforward synthesis of novel monocarbonyl curcumin analogs, their antitubercular activity, and the structure-activity relationship. The hit compound from this study, 3a, exhibits potent MIC90 values in the range of 0.2 to 0.9 μM in both ADC and CAS media.

Keywords: analogues ; aryl nitro ; curcumin ; synthesis ; tuberculosis

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Product Details of [ 99-61-6 ]

CAS No. :99-61-6 MDL No. :MFCD00007249
Formula : C7H5NO3 Boiling Point : -
Linear Structure Formula :(COH)C6H4(NO2) InChI Key :ZETIVVHRRQLWFW-UHFFFAOYSA-N
M.W : 151.12 Pubchem ID :7449
Synonyms :
m-Nitrobenzyldehyde

Calculated chemistry of [ 99-61-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.65
TPSA : 62.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : -0.18
Consensus Log Po/w : 0.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.97
Solubility : 1.6 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (Ali) : -2.4
Solubility : 0.605 mg/ml ; 0.00401 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.71
Solubility : 2.95 mg/ml ; 0.0195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 99-61-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P273-P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 UN#:N/A
Hazard Statements:H315-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99-61-6 ]

* 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.

  • Upstream synthesis route of [ 99-61-6 ]
  • Downstream synthetic route of [ 99-61-6 ]

[ 99-61-6 ] Synthesis Path-Upstream   1~57

  • 1
  • [ 5977-14-0 ]
  • [ 99-61-6 ]
  • [ 7720-39-0 ]
Reference: [1] Patent: US4918074, 1990, A,
  • 2
  • [ 99-61-6 ]
  • [ 73279-04-6 ]
Reference: [1] Patent: CN107698538, 2018, A,
  • 3
  • [ 99-61-6 ]
  • [ 16730-20-4 ]
Reference: [1] Archives of Pharmacal Research, 2011, vol. 34, # 3, p. 357 - 367
  • 4
  • [ 99-61-6 ]
  • [ 833-47-6 ]
Reference: [1] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 843 - 851
[2] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1872 - 1879
[3] Bioorganic Chemistry, 2018, vol. 78, p. 201 - 209
[4] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491
  • 5
  • [ 99-61-6 ]
  • [ 105-45-3 ]
  • [ 21881-77-6 ]
YieldReaction ConditionsOperation in experiment
95% at 70℃; for 2.5 h; Green chemistry; Enzymatic reaction General procedure: Urease (0.05 g) was added to a mixture of aldehyde (5 mmol), 1,3-dicarbonyl (5mmol), and urea (15 mmol), and the mixture was stirred at 70 °C in water, till the product precipitated. After completion of the reaction (thin-layer chromatography (TLC) monitoring, hexane:EtOAc(70:30)), cold water was added and the product was filtered to give the pure 1,4-DHP product.
95% With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10 h; In the 100 ml flask is added in a single port 0.01 µM percent Lewis acid-base dual function catalyst I (wherein Rf=CF3; R1, R2, R3, R4, R5, R6=F), 0.1 µM m formaldehyde (R7=3 - NO2- Ph), 0.1 µM methyl acetoacetate (R8=Me; R9=Me), 0.1 µM ammonium acetate, 10 ml toluene, the reaction in the 100 °C stirring for 10 hours, TLC tracking reaction to the reaction is complete. The reaction result is: product II (R7=3 - NO2- Ph; R8=Me; R9=Me) of the yield is 97percent; catalyst system used repeatedly 10 times, its catalytic performance did not decline
90% With uranyl nitrate hexahydrate; ammonium acetate In ethanol at 20℃; for 0.333333 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.
90% With Er(1,3,5-benzenetricarboxylate)(aqua)(N,N-dimethylformamide)1.1; ammonium acetate In ethanol at 70℃; for 4 h; General procedure: Ammonium acetate (1 mmol), was added to the mixture of benzaldehyde (1 equiv), and ethyl acetoacetate (1.1 equiv) in Ethanol (1.5 mL) along with an appropriate amount of Er-MOF as catalyst (20 mg). The mixture was stirred at 70 °C for 4 h. After completion of the reaction, the catalyst was removed by centrifuge. Then brine (5 mL) and EtOAc (5 mL) was added. The mixture was extracted with EtOAc and the combined organic phase were washed with saturated aqueous solution of NaHCO3 (10 mL), and brine(10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. After removal of the solvent under vacuum, the crude product was purified by column chromatography to afford the desired product, Table 1. It is found that the Er-MOF catalyst can be recovered and reused five times without considerable loss of catalyticactivity.
88% at 100℃; for 0.333333 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.
84% at 80℃; for 0.216667 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.
80% With ammonium hydroxide In ethanol at 120℃; for 0.1 h; Flow reactor General procedure: A 25 mL of stock solutioncontaining aldehyde (1eq), ethyl acetoacetate (3.4eq) 28percent ammonium hydroxide(10eq) and ethanol was prepared. Then, a stainless steel syringe was loaded,the PHD 4400 Hpsi Programmable Syringe Pump was used, and the solution streammerged in a tubular PFA micro reactor [200µL, 0.02’’ (inch = 2.54 cm) innerdiameter, 100 cm length)] and immersed in a heated oil bath at 120oC.The microreactor was equipped with a 100 psi backpressure regulator (BPR) and variableminutes of residence time were used.At the outlet of the microreactor, the pressure was released to ambient conditions and the reactionmixture was collected. Initially a flushwas preceded to ensure steady-state data collection (4x times residence time). Performingthe protocol on the 1 mmol scale, the product was collected as a stream in avial. After that the sample was transferred to a separatory funnel.10 mL of water and 20 mL of diethyl ether was added, then the aqueous layer wasremoved and the organic phase was collected and dried using Na2SO4.The solution was concentrated to obtain a yellow oil. After 10 hours indessicator with P2O5 the sample became a solid, then itwas recrystalized using heptane and diethyl ether. After drying, the solidswere weight to measure the yield.The structure of the products was determined by IR, 1HNMRand 13CNMR spectroscopy, mass analysis.
77.2% With ammonia In methanol; ethanol a)
Preparation of dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
A mixture of 75.5 g (0.50 mole) of 3-nitrobenzaldehyde, 116 g (1.00 mole) of methyl acetoacetate and 55 ml (1.50 mole) of 28percent ammonia in 150 ml of methanol is heated under reflux for 5 hr.
The precipitate is removed by filtration and the cake purified by hot washing in absolute ethanol, giving 133.5 g of a yellow powder.
M.pt.inst. (Kofler)=208° C. Yield=77.2percent
70.9% With ammonium bicarbonate In ethanol; water at 55 - 60℃; Reflux (2)
Preparation of dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
5 g meta-nitrobenzaldehyde (0.033 mol), 8 mL methyl acetoacetate (0.072 mol), 10 mL ethanol, 4 g ammonium bicarbonate (0.05 mol) and 4 mL water were mixed and stirred at 55-60° C. until no bubble formed (about 1 hour).
The mixture was continued to react under reflux for 1-2 hours, cooled, and filtered by suction.
The filter cake was dried in vacuum to produce the title product as a yellow solid (8.1 g) in a yield of 70.9percent.
70.9% With ammonium bicarbonate In ethanol; water at 55 - 60℃; for 2 - 3 h; Reflux (2)
Preparation of dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
5g meta-nitrobenzaldehyde (0.033mol), 8mL methyl acetoacetate (0.072mol), 10mL ethanol, 4g ammonium bicarbonate (0.05mol) and 4mL water were mixed and stirred at 55-60 °C until no bubble formed (about 1 hour).
The mixture was continued to react under reflux for 1-2 hours, cooled, and filtered by suction.
The filter cake was dried in vacuum to produce the title product as a yellow solid (8.1g) in a yield of 70.9percent.
60% Darkness; Reflux General procedure: To a 50-mL round-bottomed flask, ammonium acetate (0.162 g,2.10 mmol) was added to a stirring solution of 2-nitrobenzaldehydeor 3-nitrobenzaldehyde (0.254 g, 1.65 mmol) and thecorresponding alkyl acetoacetate (3.35 mmol) in methanol or2-propanol (10 mL). The reaction mixture was protected fromlight and heated under reflux for 12–24 h. After cooling, theprecipitate was filtered and purified by crystallization frommethanol or 2-propanol to afford the corresponding product.

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YieldReaction ConditionsOperation in experiment
77% With graphite oxide In neat (no solvent) at 80℃; for 2 h; General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
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  • [ 76258-20-3 ]
YieldReaction ConditionsOperation in experiment
74% With graphite oxide In water for 7 h; Reflux General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
55% With graphite oxide In water for 7 h; Reflux General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
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  • [ 99-34-3 ]
  • [ 6307-83-1 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
  • 26
  • [ 99-61-6 ]
  • [ 4403-70-7 ]
YieldReaction ConditionsOperation in experiment
53% With pyridine In methanol; ethyl acetate Step 1
Synthesis of 3-aminomethyl-phenylamine (12-1b)
3-Nitrobenzaldehyde (1.51 g) and hydroxylamine hydrochhride (1.29 g) were dissolved in methanol (100 ml), and to the solution was slowly added pyridine (2.37 g) at room temperature, followed by stirring for 18 hours.
The resulting mixture was concentrated under reduced pressure.
The residue was dissolved in ethyl acetate (30 ml), washed with water (10 ml*2) and saturated aqueous copper sulfate solution (10 ml), dried over magnesium sulfate, concentrated under reduced pressure, and then the residue was purified by column-chromatography (hexane/ethyl acetate=3/1) to yield oxime (1.66 g).
The obtained oxime was dissolved in methanol (20 ml) and to the solution was added 10percent palladium/carbon (414 mg), followed by stirring at room temperature under hydrogen atmosphere for 3 days.
The reaction mixture was filtered to remove the precipitate and the filtrate was concentrated under reduced pressure to yield the compound 12-1b (643 mg, 53percent).
1H NMR(300 MHz, DMSO-d6): δ 7.08(t, J=8.1 Hz, 1H), 6.66(m, 2H), 6.55(d, J=8.1 Hz, 1H), 2.40 (bs, 2H)
Reference: [1] Patent: US2003/153596, 2003, A1,
  • 27
  • [ 623-73-4 ]
  • [ 99-61-6 ]
  • [ 52119-38-7 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 43, p. 13237 - 13252
  • 28
  • [ 623-73-4 ]
  • [ 99-61-6 ]
  • [ 7772-99-8 ]
  • [ 52119-38-7 ]
Reference: [1] Patent: EP946528, 2003, B1,
[2] Patent: US6187797, 2001, B1,
  • 29
  • [ 99-61-6 ]
  • [ 1877-77-6 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With nickel boride In water at 20℃; for 0.0833333 h; Green chemistry
Stage #2: With sodium tetrahydroborate In water at 20℃; for 0.133333 h; Green chemistry
General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction,aqueous solution of KOH (2 percent, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 percent yield (0.088 g, Table 2, entry 1).
92% With sodium tetrahydroborate; copper In water at 80℃; for 0.0666667 h; Green chemistry General procedure: In a round-bottom flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Cu NPs (0.0095 g,15 mmol percent) was then added, and the mixture was stirredfor 3 min at 80 °C. Afterward, NaBH4 (0.076 g, 2 mmol)was added portion wisely (two portions) with the intervalof 2 min, and the resulting mixture was continued to stirringat 80 °C. TLC monitored the progress of the reaction(n-hexane/EtOAc: 5/2). After completion of the reaction,Cu NPs was separated by filtration, and the mixture wasextracted with EtOAc (2 × 5 mL). The organic layer wasthen dried over anhydrous Na2SO4. Evaporation of the solventaffords the pure liquid aniline in 91 percent yield (0.085 g,Table 2, entry 1).
91% With sodium tetrahydroborate In water at 60 - 70℃; for 0.333333 h; Green chemistry General procedure: In a round-bottom flask (10 mL) containing 2 mL water, a mixture of nitrobenzene (0.123 g, 1 mmol) and Fe3O4SiO2Cu–Ni–Fe–Cr LDH (10 mg) was prepared and the resulting mixture was stirred for 5 min. Next, NaBH4(0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min under oil bath conditions (60–70 °C). TLC monitored the progress of the reaction (eluent, n-hexane/EtOAc: 5/2). After completion of the reduction reaction, the mixture was cooled to the room temperature. EtOAc (3 mL) was then added and the resulting mixture was again stirred for 10 min. The magnetic nanocatalyst was separated by an external magnet followed by extraction with EtOAc (2 × 5 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent afforded the pure liquid aniline in 95percent yield (Table 2, entry 1).
90%
Stage #1: at 20℃; for 0.05 h; Green chemistry
Stage #2: With glycerol In water at 20℃; for 1 h; Green chemistry
General procedure: In a round-bottom flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (1 mmol, 0.123 g) and H2O(2 mL) was prepared. Fe3O4(at)APTMS(at)ZrCp2 (7 mg)was then added and the resulting mixture was stirred for 3 min. Next, glycerol (2 mmol) was added and the reaction mixture was stirred for 40 min at room temperature. TLC monitored the progress of the reaction (eluent, n-hexane/EtOAc: 5/2). After completion of the reaction, the catalyst mixture was extracted with EtOAc (2 × 5 mL). Drying organiclayer over anhydrous Na2SO4followed by evaporation of the solvent affords pure liquid aniline in 96percent yield (0.089 g,Table 3, entry 1).

Reference: [1] Journal of the Iranian Chemical Society, 2015, vol. 12, # 7, p. 1221 - 1226
[2] Journal of Chemical Research, 2006, # 8, p. 542 - 544
[3] Dalton Transactions, 2016, vol. 45, # 36, p. 14230 - 14237
[4] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5575 - 5580
[5] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 4, p. 679 - 684
[6] Journal of the Iranian Chemical Society, 2016, vol. 13, # 8, p. 1487 - 1492
[7] Journal of the Iranian Chemical Society, 2018, vol. 15, # 12, p. 2821 - 2837
[8] Journal of the Iranian Chemical Society, 2017, vol. 14, # 12, p. 2649 - 2657
[9] Applied Organometallic Chemistry, 2017, vol. 31, # 12,
[10] Organometallics, 2016, vol. 35, # 4, p. 503 - 512
[11] Mem.Coll.Sci.Kyoto&lt;A&gt;, vol. 11, p. 5[12] Chem. Zentralbl., 1928, vol. 99, # I, p. 2391
[13] Mem.Coll.Sci.Kyoto&lt;A&gt;, vol. 11, p. 5[14] Chem. Zentralbl., 1928, vol. 99, # I, p. 2391
[15] Patent: US2273564, 1939, ,
[16] Journal of Catalysis, 2011, vol. 284, # 2, p. 176 - 183
[17] Journal of the American Chemical Society, 2012, vol. 134, # 39, p. 16143 - 16146
[18] Catalysis Today, 2013, vol. 213, p. 93 - 100
[19] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[20] Angewandte Chemie - International Edition, 2017, vol. 56, # 33, p. 9747 - 9751[21] Angew. Chem., 2017, vol. 129, p. 9879 - 9883,5
[22] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
[23] Journal of the Iranian Chemical Society, 2018, vol. 15, # 12, p. 2821 - 2837
  • 30
  • [ 99-61-6 ]
  • [ 1877-77-6 ]
  • [ 116800-10-3 ]
  • [ 1709-44-0 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1983, vol. 22, # 8, p. 664 - 670
  • 31
  • [ 67-56-1 ]
  • [ 99-61-6 ]
  • [ 51513-29-2 ]
  • [ 35531-57-8 ]
  • [ 2345-56-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 24, p. 4545 - 4556
  • 32
  • [ 67-56-1 ]
  • [ 99-61-6 ]
  • [ 51513-29-2 ]
  • [ 35531-57-8 ]
  • [ 2345-56-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 24, p. 4545 - 4556
  • 33
  • [ 2033-24-1 ]
  • [ 99-61-6 ]
  • [ 1664-57-9 ]
YieldReaction ConditionsOperation in experiment
72% With formic acid; triethylamine In N,N-dimethyl-formamideLarge scale General procedure: NEt3 (56.6 g, 0.56 mol) was added dropwise to stirred formicacid (64.4 g, 1.4 mol) at 5 8C. To the resulting reagent were addedDMF (150 ml), Meldrum’s acid (57.6 g, 0.4 mol) and aldehyde 2a–c(60.4 g, 0.4 mol). The reaction mixture was heated at reflux for 4 h.The solvent was evaporated under vacuum.The residue was triturated with water (1000 ml) and acidifiedwith conc. aq HCl to pH = 2. The formed product was filtered off,dried on air, and crystallized from EtOAc (3a) or CCl4 (3b,c) toobtain the pure material.
Reference: [1] Journal of Fluorine Chemistry, 2015, vol. 171, p. 174 - 176
[2] Archiv der Pharmazie, 2011, vol. 344, # 12, p. 840 - 842
  • 34
  • [ 99-61-6 ]
  • [ 14755-02-3 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2047
[2] Chemische Berichte, 1889, vol. 22, p. 2354
  • 35
  • [ 110-89-4 ]
  • [ 555-68-0 ]
  • [ 99-61-6 ]
  • [ 1664-54-6 ]
Reference: [1] Patent: US4769447, 1988, A,
  • 36
  • [ 99-61-6 ]
  • [ 1664-54-6 ]
Reference: [1] Chemische Berichte, 1935, vol. 68, p. 184,187
  • 37
  • [ 99-61-6 ]
  • [ 60200-06-8 ]
Reference: [1] Patent: CN104230767, 2016, B,
  • 38
  • [ 99-61-6 ]
  • [ 74-89-5 ]
  • [ 19499-61-7 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 80℃; for 24 h; Molecular sieve; Sealed tube
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 24 h;
General procedure: The desired nitro-substituted benzaldehyde (1 eq, 13.2 mmol, 2.0 g), methylamine (40percent watersolution, 1.1 eq, 14.5 mmol, 0.95 mL) and molecular sieves (3A, 100 mg) were introduced in a screw cap vialand the mixture was heated at 80°C for 24h. After cooling to RT, the mixture was diluted with chloroform (3mL) and filtered. The solvent was removed by rotary evaporation and the crude obtained was redissolved inmethanol (30 mL) and cooled to 0 °C. NaBH4 (1.1 eq, 14.5 mmol, 550 mg) was added in three portions andthe resultant mixture allowed warming to RT and reacting for 24 h. The mixture was then quenched with aq.NH4OH 5percent (10 mL) and the solvent was concentrated by rotary evaporation. The obtained aqueous layer wasextracted with CH2Cl2 (3 x 10 mL). The combined organic extracts were dried over Na2SO4, filtered and thefiltrate was concentrated by rotary evaporation. The residue was purified by silica gel flash chromatographyor distillation under vacuum to give the title compound.
Reference: [1] Molecules, 2017, vol. 22, # 12,
[2] Patent: WO2013/140347, 2013, A1, . Location in patent: Page/Page column 48-49
[3] Patent: US2015/51257, 2015, A1, . Location in patent: Paragraph 0519-0520
  • 39
  • [ 593-51-1 ]
  • [ 99-61-6 ]
  • [ 19499-61-7 ]
YieldReaction ConditionsOperation in experiment
67% With sodium tetrahydroborate; titanium(IV)isopropoxide; triethylamine In ethanol at 20℃; for 24 h; A mixture of 3-nitrobenzaldehyde (1.50 g), methylamine hydrochloride (1.35 g), tetraisopropoxytitanium (5.90 mL) and triethylamine (2.79 mL) in ethanol (15 mL) was stirred at room temperature for 12 hrs. To the reaction mixture was added sodium borohydride (0.57 g) and the mixture was stirred at room temperature for 12 hrs. To the reaction mixture was added 2M aqueous ammonia. The resulting inorganic salt was removed by filtration and washed with dichloromethane. The organic layer was separated and the aqueous layer was extracted. with dichloromethane. The organic layers were combined and washed with 1N hydrochloric acid. The aqueous layer was basified with 2N aqueous sodium hydroxide, extracted with dichloromethane and dried (MGSO4). The solvent was evaporated to give the title compound (1.11 g, yield 67percent). 1H NMR (300 MHz, CDC13) 8 ppm: 2.47 (s, 3 H), 3.86 (s, 2 H), 7.49 (t, J = 7.8 Hz, 1 H), 7.62-7. 71 (m, 1 H), 8.06-8. 15 (m, 1 H), 8.20 (t, J = 1.7 Hz, 1 H).
Reference: [1] Patent: WO2004/46107, 2004, A1, . Location in patent: Page 188
[2] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
[3] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 16, p. 2527 - 2531
[4] Patent: WO2006/40526, 2006, A1, . Location in patent: Page/Page column 104
  • 40
  • [ 99-61-6 ]
  • [ 19499-61-7 ]
YieldReaction ConditionsOperation in experiment
27% With methylamine hydrochloride; sodium cyanoborohydride; triethylamine In methanol Example 42
Synthesis of N-(3-nitrophenylmethyl)methylamine
To a mixture of sodium cyanoborohydride (2.52 g), triethylamine (18.7 ml), methylamine hydrochloride (5.42 g) and methanol (660 ml), m-nitrobenzaldehyde (10.10 g) was added dropwise over 20 minutes at room temperature and the resulting mixture was stirred at room temperature for 20 h.
The pH of the reaction mixture was adjusted to 2 by addition of 10percent HCl and the methanol was distilled off under reduced pressure.
The residue was washed with chloroform and a 10percent aqueous potassium hydroxide solution was added to the aqueous layer for pH adjustment to 12, and the mixture was extracted with chloroform.
The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure.
The resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=95:5) to give 3.0 g of the titled compound (yield, 27percent).
1H-NMR(CDCl3) δ: 1.52(1H,brs), 2.47(3H,s), 3.87(2H,s), 7.50(1H,dd, J=7.8, 7.8 Hz), 7.68(1H,d J=7.8 Hz), 8.20(1H,d, J=7.8 Hz), 8.44(1H,s)
Reference: [1] Patent: US6534546, 2003, B1,
[2] Organic Process Research and Development, 2005, vol. 9, # 6, p. 837 - 842
[3] Organic Process Research and Development, 2005, vol. 9, # 6, p. 837 - 842
  • 41
  • [ 99-61-6 ]
  • [ 355134-13-3 ]
YieldReaction ConditionsOperation in experiment
82% at 65℃; for 1 h; To a solution of 3-nitrobenzaldehyde (1.0 g, 6.6 mmol) inconcentrated sulfuric acid (4.0 mL) was added N-bromosuccinimide (1.4 g, 7.9 mmol) in small portions at room temperature andthen heated to 65 C for 1 h. After cooling to the room temperature,the solution was poured into ice water and the precipitate wasfiltered. The crude product was dried over Na2SO4 and recrystallized from EtOAc/petroleum ether (1/10) to obtain 13 (1.3 g, 82percent) aswhite crystals. 1H NMR (300 MHz, DMSO-d6) d: 10.09 (s, 1H),8.79e8.55 (m, 2H), 8.51 (s, 1H).
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5235 - 5244
[2] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[3] European Journal of Medicinal Chemistry, 2016, vol. 116, p. 46 - 58
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4512 - 4513
[5] Patent: WO2009/153313, 2009, A1, . Location in patent: Page/Page column 185
  • 42
  • [ 99-61-6 ]
  • [ 17557-76-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 26
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 26
  • 43
  • [ 541-50-4 ]
  • [ 99-61-6 ]
  • [ 14205-39-1 ]
  • [ 74936-72-4 ]
YieldReaction ConditionsOperation in experiment
83% With polyphosphoric acid In ethanolReflux; Inert atmosphere General procedure: A solution of ethyl acetoacetate (3) (576 mg, 4.4 mmol),4-fluoro benzaldehyde (1a) (500 mg, 4 mmol) and thiourea(2) (306 mg, 4 mmol) in ethanol (5 mL) was heated under reflux (78-80 °C) in the presence of poly phosphoric acid(1350 mg, 4 mmol) for 12 h under nitrogen. The progress ofthe reaction was monitored by TLC (hexane: ethyl acetate,1:1 v/v). The reaction mixture, after being concentrated under vacuum at 60 °C, cooled to room temperature, it was poured into crushed ice (10 g) and stirred for 5-10 min. The solid separated was then filtered under suction, washed withice-cold water (20 mL) and then recrystallized from hot ethanol to afford pure product 4a (2.08 g, 88percent). The same experimental procedure was adopted for the preparation of remaining title compounds (4b-l & 9) (Scheme 1 & 2, Table3).
Reference: [1] Combinatorial Chemistry and High Throughput Screening, 2015, vol. 18, # 9, p. 862 - 871
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  • [ 22886-02-8 ]
  • [ 99-61-6 ]
  • [ 80612-98-2 ]
  • [ 74936-72-4 ]
Reference: [1] Patent: US5633383, 1997, A,
  • 45
  • [ 173407-10-8 ]
  • [ 99-61-6 ]
  • [ 80612-98-2 ]
  • [ 74936-72-4 ]
Reference: [1] Patent: US5633383, 1997, A,
  • 46
  • [ 99-61-6 ]
  • [ 74936-72-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 8, p. 1579 - 1589
[2] Patent: US2014/45896, 2014, A1,
[3] Patent: EP2703398, 2014, A1,
[4] Molecules, 2014, vol. 19, # 1, p. 1344 - 1352
  • 47
  • [ 99-61-6 ]
  • [ 84459-32-5 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 48
  • [ 99-61-6 ]
  • [ 77976-08-0 ]
  • [ 108159-96-2 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 2, p. 339 - 344
  • 49
  • [ 99-61-6 ]
  • [ 105-45-3 ]
  • [ 90096-33-6 ]
  • [ 89226-75-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 50
  • [ 99-61-6 ]
  • [ 89226-49-3 ]
  • [ 14205-39-1 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 51
  • [ 99-61-6 ]
  • [ 93793-83-0 ]
Reference: [1] Patent: CN107698538, 2018, A,
  • 52
  • [ 99-61-6 ]
  • [ 199177-26-9 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4512 - 4513
[2] European Journal of Medicinal Chemistry, 2016, vol. 116, p. 46 - 58
  • 53
  • [ 99-61-6 ]
  • [ 100427-51-8 ]
  • [ 132866-11-6 ]
Reference: [1] Patent: WO2008/107797, 2008, A2,
  • 54
  • [ 99-61-6 ]
  • [ 555-68-0 ]
  • [ 19883-74-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
  • 55
  • [ 99-61-6 ]
  • [ 123524-52-7 ]
Reference: [1] Patent: CN105461691, 2016, A,
  • 56
  • [ 99-61-6 ]
  • [ 157837-31-5 ]
Reference: [1] Patent: WO2015/144614, 2015, A1,
[2] Patent: EP3144307, 2017, A1,
  • 57
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  • [ 734529-57-8 ]
Reference: [1] Patent: CN108976141, 2018, A,
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