- Synthesis method of N-methyl o-fluoroaniline
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The invention relates to the field of preparation of pesticide and medical intermediates, and in particular, relates to a preparation method of N-methyl o-fluoroaniline, wherein the preparation method comprises the following steps: by taking o-fluoroaniline as a raw material and dimethyl carbonate as a reaction raw material and a reaction solvent, carrying out heat preservation reaction under the action of a basic catalyst; and after the reaction is finished, filtering to remove the catalyst, carrying out rectification separation on filtrate, and separating the solvent dimethyl carbonate from the product. Compared with the prior art, the novel synthesis method of N-methyl o-fluoroaniline provided by the invention has the following effective effects: only one-step reaction is needed, the selectivity is extremely high, the product quality is good, the selected methylation reagent dimethyl carbonate is low in toxicity, green and safe, the output of three wastes is low, and the novel synthesis method of N-methyl o-fluoroaniline is a green chemical process with extremely competitive power.
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Paragraph 0018; 0024; 0026-0041
(2021/05/29)
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- Preparation method for coproducing N-methyl-2-fluoroaniline and crystallized sulfanilamide
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The invention discloses a preparation method for co-production of N-methyl-2-fluoroaniline and crystallized sulfanilamide. The preparation method comprises the following steps: S1, taking o-fluoroaniline, p-acetamidobenzenesulfonyl chloride and an acid-binding agent for condensation reaction to obtain a substance A; S2, performing methylation reaction on the substance A, a methylation reagent andan alkaline substance, and then performing amino deprotection to obtain a substance B; finally, subjecting the substance B and an aminating agent to be subjected to an ammonolysis reaction to obtain N-methyl-2-fluoroaniline and crystallized sulfanilamide. According to the preparation method, o-fluoroaniline and p-acetamidobenzenesulfonyl chloride are taken as raw materials, two substances, namelyN-methyl-2-fluoroaniline and crystallized sulfanilamide, are synchronously prepared, and the yield is relatively high.
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Paragraph 0051; 0055; 0060; 0064-0065; 0069-0070; 0074
(2020/07/27)
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- Synthesis method of N-methyl o-fluoroaniline
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The invention discloses a synthesis method of N-methyl o-fluoroaniline, which comprises the following steps: an amidation reaction: by using o-fluoroaniline as a raw material, mixing o-fluoroaniline with toluene and formic acid, heating to react, and dehydrating while reacting to obtain N-(2-fluorophenyl) formamide; a methylation reaction: taking N-(2-fluorophenyl) formamide as a raw material, adding dimethyl carbonate and a catalyst, putting into an autoclave, and heating to carry out the methylation reaction so as to obtain N-methyl-N-formyl-2-fluoroaniline; and a hydrolysis reaction: takingN-methyl-N-formyl-2-fluoroaniline as a raw material, mixing the N-methyl-N-formyl-2-fluoroaniline with water and sulfuric acid, carrying out hydrolysis, and carrying out post-treatment to obtain theN-methyl o-fluoroaniline. The method has the advantages of easily available raw materials, low raw material cost, mild reaction conditions, greenness, safety, high total yield (up to 90%), and great industrial application prospect.
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Paragraph 0034; 0041-0043; 0044; 0049; 0050; 0051; 0056-0057
(2020/09/23)
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- Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: Scope and mechanism
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A series of molybdenum pincer complexes has been shown for the first time to be active in the catalytic hydrogenation of amides. Among the tested catalysts, Mo-1a proved to be particularly well suited for the selective C-N hydrogenolysis of N-methylated formanilides. Notably, high chemoselectivity was observed in the presence of certain reducible groups including even other amides. The general catalytic performance as well as selectivity issues could be rationalized taking an anionic Mo(0) as the active species. The interplay between the amide CO reduction and the catalyst poisoning by primary amides accounts for the selective hydrogenation of N-methylated formanilides. The catalyst resting state was found to be a Mo-alkoxo complex formed by reaction with the alcohol product. This species plays two opposed roles-it facilitates the protolytic cleavage of the C-N bond but it encumbers the activation of hydrogen.
- Leischner, Thomas,Artús Suarez, Lluis,Spannenberg, Anke,Junge, Kathrin,Nova, Ainara,Beller, Matthias
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p. 10566 - 10576
(2019/12/02)
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- Manufacturing method for halogen substituted N-methylaniline
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The present invention relates to a method for manufacturing halogen-substituted N-methylaniline from halogen-substituted aniline. When halogen-substituted N-methylaniline is manufactured by using the method of the present invention, it is possible to manufacture halogen-substituted N-methylaniline without using existing methoxide sodium which has low chemical stability and is expensive, by using a low-cost base having excellent chemical stability such as potassium hydroxide or sodium hydroxide. Therefore, it is possible to reduce costs in a manufacturing process and to produce N-methylaniline with a high yield and high purity, thereby being useful for mass production as a raw material for herbicide metamifop synthesis.COPYRIGHT KIPO 2019
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Paragraph 0025-0029; 0031-0032; 0033; 0034; 0043
(2019/09/05)
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- Synthesis method of N-methyl-2-fluoroaniline
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The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of N-methyl-2-fluoroaniline. The synthesis method comprises the following steps: step one, mixing 2-fluoroaniline with concentrated hydrochloric acid, adding a sodium nitrite solution and carrying out thermal reaction to obtain 2-fluoroaniline diazonium salt; step two, adding the 2-fluoroaniline diazonium salt into a methylamine aqueous solution, and carrying out thermal reaction and post treatment to obtain the N-methyl-2-fluoroaniline. According to the method, the N-methyl-2-fluoroaniline with high yield and high selectivity can be obtained by taking the 2-fluoroaniline as a raw material, carrying out diazotization reaction on the 2-fluoroaniline and then carrying out high temperature reaction on the methylamine aqueous solution and a reactant; reaction raw materials are cheap and easily obtained; the process is reasonable, advanced and feasible; the obtained N-methyl-2-fluoroaniline has the advantages of high purity, good quality and capability of being industrially produced on a large scale.
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Paragraph 0023-0048
(2019/01/08)
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- The design, synthesis and evaluation of selenium-containing 4-anilinoquinazoline hybrids as anticancer agents and a study of their mechanism
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Inhibition of tubulin polymerization is one of the significant strategies in the treatment of cancer. Inspired by the excellent antitumor activity of EP128495 and the beneficial biological activities of selenium compounds, a series of new selenium-containing 4-anilinoquinazoline hybrids were synthesized and evaluated as tubulin polymerization inhibitors. An anti-proliferative activity assay showed that most of the compounds inhibited human sensitive cancer cells at low nanomolar concentrations. A mechanism study revealed that the optimal compound 5a disrupted microtubule dynamics, decreased the mitochondrial membrane potential and arrested HeLa cells in the G2/M phase, finally resulting in cellular apoptosis.
- An, Baijiao,Zhang, Shun,Hu, Jinhui,Pan, Tingting,Huang, Ling,Tang, Johnny Cheuk-On,Li, Xingshu,Chan, Albert S. C.
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p. 4701 - 4714
(2018/07/03)
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- A N - methyl [...] aniline synthesis method (by machine translation)
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The invention discloses a N - methyl [...] aniline synthesis method, comprises the following steps: comprises the following steps: (1) in order to [...] aniline as raw materials, adding toluene, paraformaldehyde and catalyst A, thermal insulation reaction after dehydration, post-processing to obtain N - methylene [...] aniline; (2) the N - methylene [...] aniline, catalyst B into a high-pressure, nitrogen after the replacement, the hydrogen gas and maintain a certain pressure, the temperature of the hydrogenation reaction, after treatment shall be N - methyl [...] aniline. The method can have easy availability of raw materials, mild reaction conditions, material cost is relatively low, to avoid impurity inclusion agent such enormous advantages, has great prospects for industrial application. (by machine translation)
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Paragraph 0020; 0030; 0033-0035; 0038-0040; 0043-0045; 0048
(2018/05/16)
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- N-Methylation of Amines with Methanol Catalyzed by a Cp?Ir Complex Bearing a Functional 2,2′-Bibenzimidazole Ligand
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A new type of Cp?Ir complex bearing a functional 2,2′-bibenzimidazole ligand was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs2CO3).
- Liang, Ran,Li, Shun,Wang, Rongzhou,Lu, Lei,Li, Feng
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supporting information
p. 5790 - 5793
(2017/11/10)
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- PHENYLACETIC ACID COMPOUND
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A compound represented by formula (I), wherein R1 represents a hydrogen atom, etc., R2 and R3 each independently represents a hydrogen atom, optionally oxidized C1-4 alkyl group or optionally protected hydroxyl group, or R2 and R3 taken together represent optionally oxidized C2-5 alkylene group, R4 represents an optionally oxidized C1-6 alkyl group, etc., R5 represents an optionally oxidized C1-6 alkyl group, etc., R6 represents an optionally oxidized C1-6 alkyl group, etc., m represents 0 or an integer from 1 to 3, n represents 0 or an integer from 1 to 4, and i represents 0 or an integer from 1 to 7.
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Page/Page column 26
(2010/05/13)
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- Highly specific N-monomethylation of primary aromatic amines
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A synthetic methodology for the specific conversion of primary aromatic amines into their N-monomethyl derivatives under very mild conditions is presented. Anilines are treated with 4-nitrobenzenesulfonyl (nosyl) chloride to generate the corresponding sulfonamides 2 in high yields. The subsequent N-methylation reaction of the sulfonamides 2 with a solution of diazomethane is rapid and quantitative. Removal of the nosyl protecting group is readily carried out using the reagent system mercaptoacetic acid/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording the N-monomethylated aromatic amines 4. The procedure is convenient, efficient, and gives rise to the N-monomethyl-anilines exclusively.
- Le Pera, Adolfo,Leggio, Antonella,Liguori, Angelo
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p. 6100 - 6106
(2007/10/03)
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- INDOLE DERIVATIVE COMPOUNDS AND DRUGS CONTAINING THE COMPOUNDS AS THE ACTIVE INGREDIENT
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An indole derivative compound represented by formula (I) (wherein the symbols in the formula are as mentioned in the specification) and a salt thereof Since the compounds represented by formula (I) binds to PGD2 receptors and shows antagonistic activity, they are believed to be useful for prevention and/or treatment of diseases such as allergic disease (such as allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma and food allergy), systemic mastocytosis, systemic mast cell activating disorder, anaphylaxis shock, airway contraction, urticaria, eczema, diseases accompanied by itch (such as atopic dermatitis, urticaria), diseases (such as cataract, retinal detachment, inflammation, infection and sleep disorder) which are generated secondarily as a result of behavior accompanied by itch (such as scratching and beating), inflammation, chronic obstructive pulmonary diseases, ischemic reperfusion injury, cerebrovascular accident, autoimmune disease, chronic articular rheumatism, pleuritis, ulcerative colitis and irritable bowel syndrome.
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Page/Page column 93-94
(2010/02/14)
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- INDOLE DERIVATIVES
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Compounds represented by formula (I) wherein all symbols represent the same meanings as described in specification. and salts thereof. Since the compound represented by the formula (I) binds and antagonizes to DP receptor, it is useful for the prevention or treatment against the disease such as allergic disorder, diseases accompanied with itching, secondary diseases generated by behaviors caused by itching, inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, pleuritis complicated by rheumatoid arthritis, cerebrovascular disease, and ulcerative colitis.
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- INDOLE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
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Indole derivatives represented by formula (I) ???wherein all symbols represent the same as that in specification), production methods thereof, and DP receptor antagonist comprising them as active ingredients. Since the compounds of formula (I) binds and antagonizes to DP receptor, they are useful for the prevention and/or treatment against allergic diseases, diseases accompanied with itching, secondary diseases generated by behaviors caused by itching, inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, cerebrovascular disorder, pleuritis complicated by rheumatoid arthritis, ulcerative colitis.
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- CARBOXYOIC ACID COMPOUNDS AND DRUGS CONTAINING THE COMPOUNDS AS THE ACTIVE INGREDIENT
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A carboxylic acid compound represented by formula (I): (meanings of the symbols in the formula are as mentioned in the specification) and a pharmaceutical agent comprising the compound. Since the compound represented by formula (I) binds to a DP receptor and shows antagonistic activity for the DP receptor, it is useful for prevention and/or treatment of diseases such as allergic disease (such as allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma and food allergy), systemic mastocytosis, disorders accompanied by systemic mast cell activation, anaphylaxis shock, bronchoconstriction, urticaria, eczema, diseases accompanied by itch (such as atopic dermatitis and urticaria), diseases (such as cataract, retinal detachment, inflammation, infection and sleeping disorders) which is generated secondarily as a result of behavior accompanied by itch (such as scratching and beating), inflammation, chronic obstructive pulmonary diseases, ischemic reperfusion injury, cerebrovascular accident, chronic rheumatoid arthritis, pleurisy, ulcerative colitis and the like.
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- 3-(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl) -3-hydroxybenzyl)-N-alkyl-N-arylbenzamides: Potent, non-peptidic agonists of both the μ and δ opioid receptors
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Opioid analgesics with both μ and δ opioid receptor activation represent a new approach to the treatment of severe pain with an improved safety profile. Compounds with this profile may exhibit strong analgesic properties due to μ agonism, with a reduced side effect profile resulting from δ agonism. Replacing the p-diethylamide of the known potent δ opioid receptor selective agonist BW373U86 with a m-diethylamide resulted in a compound with agonist activity at both the μ and δ opioid receptors. Modifying the amide to an N-methyl-N-phenylamide increased agonist potency at both receptors. A series of 3-(αR)-α((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl) -3-hydroxybenzyl)-N-alkyl-N-arylbenzamides have been made to explore the structure-activity relationship (SAR) around the N-methyl-N-phenylamide. Several potent agonists of both the μ and δ opioid receptors have been identified, including (+)-3-((αR)-α ((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3- hydroxybenzyl)-N-(4-flourophenyl)-N-methylbenzamide (23), which has EC50 values of 0.67 and 1.1 nM at the μ (guinea pig ileum assay) and δ (mouse vas deferens assay) opioid receptors, respectively.
- Bishop, Michael J.,Garrido, Dulce M.,Boswell, G. Evan,Collins, Mark A.,Harris, Philip A.,McNutt, Robert W.,O'Neill, Scott J.,Wei, Ke,Chang, Kwen-Jen
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p. 623 - 633
(2007/10/03)
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- Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization
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The development of a new method for the regioselective synthesis of functionalized indoles and six-membered benzo-fused N-, O-, and S-heterocycles is reported. The key step involves the generation of a benzyne-tethered vinyl or aryllithium compound that undergoes a subsequent intramolecular anionic cyclization. Reaction of the organolithium intermediates with selected electrophiles allows the preparation of a wide variety of indole, tetrahydrocarbazole, dihydrofenantridine, dibenzopyran, and dibenzothiopyran derivatives. Finally, the application of this strategy to the appropriate starting materials allows the preparation of some tryptamine and serotonin analogues.
- Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Fernandez, Yolanda
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p. 2034 - 2046
(2007/10/03)
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- N-phenylglycinamide CCK antagonists and pharmaceutical compositions containing them
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Compounds of formula: STR1 in which R1 represents a hydrogen atom, an alkyl or alkoxycarbonyl radical or a phenyl radical, optionally substituted, R2 represents an alkoxy, optionally substituted cycloalkyloxy, cycloalkylalkyloxy, phenylalkyloxy, polyfluoroalkyloxy or cinnamyloxy radical or a radical --NR5 R6, R3 represents a phenylamino radical in which the phenyl ring is optionally substituted, an optionally substituted phenyl radical or a naphthyl, indolyl or quinolyl radical, R4 represents a substituted phenyl radical, R5 and R6, which may be identical or different, represent a hydrogen atom or an alkyl, optionally substituted phenyl, indanyl, cycloalkylalkyl, cycloalkyl or phenylalkyl radical, or alternatively R5 and R6, together with the nitrogen atom to which they are attached, form a heterocycle, their preparation and medicinal products containing them.
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- ETHER DERIVATIVES HAVING 5-LIPOXYGENASE INHIBITORY ACTIVITY
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The invention concerns ether derivatives of the formula I Q1?X?Ar?Q2 wherein Q1 is an optionally substituted 9-, 10- or 11-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur; X is oxy, thio, sulphinyl or sulphonyl; Ar is optionally substituted phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazoiediyl, thiadiazoiediyl or oxadiazolediyl; and Q2 is selected from the groups of the formulae II and III: wherein R1 is hydrogen, (2-5C)alkanoyl or optionally substituted benzoyl; R2 is (l-4C)alkyl; and R3 is hydrogen or (l-4C)alkyl; or R2 and R3 are linked to form a methylene, vinylene, ethylene or trimethylene group; or a pharmaceutically-acceptable salt thereof; processes for their preparation; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
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- N-phenyl-N-acetamidoglycinamides, their preparation and medicaments containing them
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Compounds of formula: STR1 in which R1 represents a hydrogen atom or an alkyl, alkoxycarbonyl or an unsubstituted or substituted phenyl radical, R2 represents a hydrogen atom or an unsubstituted or substituted alkyl radical, R3 represents an alkyl, phenylalkyl, indanyl, cycloalkylalkyl or an unsubstituted or substituted phenyl radical, or R2 and R3 form a heterocycle together with the nitrogen atom to which they are attached, and R4 represents an unsubstituted or substituted phenyl radical, a naphthyl, indolyl or quinolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted, their preparation and medicaments containing them.
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