Tag: M.W=100-200

Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Stage 1: 5-nitro-isoindoline (I-12) A solution of isoindoline (3.9 g, 32.8 mmol, 1.0 eq.) in dichloromethane (20 mL) was stirred below -20 C. with exclusion of moisture while adding dropwise sulphuric acid (98%, 16.0 mL). The 2-layer mixture was allowed to reach 20 C. and then dichloromethane was removed under vacuum. The resulting pale brown solution was stirred and kept below 20 C. while adding nitric acid (70%, 3.9 mL) dropwise. The resulting pale orange-red solution was added with stirring to ice/water (300 mL) and tert-butyl methyl ether (100 mL). Sodium hydrogen carbonate (59 g) was added in portions and finally 4M aqueous sodium hydroxide (10 mL). The layers were separated and the aqueous phase extracted with tert-butyl methyl ether (4*150 mL). The combined organic phases were dried (sodium sulphate) and evaporated giving a red-brown gum (4.6 g, 85%) which was used in the next stage without purification. 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 8.05-8.19 (m, 2H) 7.38 (d, J=8.83 Hz, 1H) 4.32 (s, 4H) 2.14 (br. s., 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindoline, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; US2010/119479; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.59 2-((2-(2-(Heptan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (7C) Grey powder, mp 84-85 C, 85% yield; 1H NMR (400 MHz, DMSO-d6): delta 1.19-1.29 (m, 8H, CH2), 1.92 (s, 3H, CH3), 2.20-2.28 (t, 3H, CH3), 3.78 (s, 2H, CH2, thiazolidinone), 5.53 (s, 2H, ArCH2), 7.88-7.89 (m, 4H, Ar).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, molecular formula is C9H7NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 1-Methylisatin

General procedure: First phenyl acetylene (1 mmol) was stirred with Et3N (1 mmol) in CH3CN (5 mL) at room temperature. After 15-20 min, N-methyl isatin (1 mmol) and InBr3 (15 mol%) was added and the reaction mixture was stirred for 16-18h. When N-methyl isatin was completely consumed as indicated by TLC, phenacyl bromide (1 mmol) was added and the reaction mixture was stirred until the reaction reached completion, as evidenced by TLC. Acetonitrile was distilled out under reduced pressure and the residue was purified by silica gel (mesh 60-120) chromatography (hexane-EtOAc) to afford the corresponding products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-74-4, its application will become more common.

Reference:
Article; Siddiqui; Rahila; Shamim, Shayna; Rai, Pragati; Shireen; Waseem, Malik A.; Abumhdi, Afaf A.H.; Tetrahedron Letters; vol. 54; 51; (2013); p. 6991 – 6994;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6341-92-0 as follows.

General procedure: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2×10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 56341-37-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 56341-37-8 name is 6-Chlorooxindole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 3Preparation of 6-chloro-5-(chloroacetyl) oxindole :Charged with 500 ml of ethylene dichloride and A1C13 (250gm) in a 3 litre there-neck flask under nitrogen atmosphere at 25 to 30C. Add 84.19 gm of chloroacetyl chloride slowly at RT controlling the exotherm and stirred for 30 minutes.Contents are further added with 100 gm of 6- chloro-oxindoie at 35-37C in an hour. Stirring is continued at 35-37C for 10-12 hrs.Cool gradually to 0 to 5C and pour into ice, and water under stirring over 30 minutes. Stir for 30 minutes, remove ethylene dichloride by distlation under vacuum, cool the mass and filter off the product wash with water till it is neutral. Purify the product using 1,4- dioxane if required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chlorooxindole, and friends who are interested can also refer to it.

Reference:
Patent; ARCH PHARMALABS LIMITED; GHOGARE, Bhausaheb Nana; DESHPANDE, Uday K.; PAI, Ganesh Gurpur; MANDAL, Arun Kanti; CHARANJIT, Sehgal; NEHA, Dixit Akshaya; WO2012/20424; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 199328-10-4, name is Methyl Oxindole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl Oxindole-5-carboxylate

Into a 50-mL round-bottom flask was placed methyl 2-oxo-2,3-dihydro-1H- indole-5-carboxylate (800 mg, 4.18 mmol, 1.00 equiv) and methanol (10 mL). This was followed by the addition of a solution of NaOH (670 mg, 16.75 mmol, 4.00 equiv) in water (10 mL) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The mixture was then concentrated under vacuum and the residue taken up in 20 mL of H2O. This was washed with 2×5 mL of dichloromethane. The pH was adjusted to 4 with hydrochloric acid (1 N) and extracted with 5×50 mL of ethyl acetate and the organic layers combined. Concentration resulted in 592 mg (80%) of 2-oxo-2,3-dihydro- 1H-indole-5-carboxylic acid as a yellow solid

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., Safety of 2-Methylindoline

Preparation 2 Synthesis of N-trifluoroacetyl-2-methylindoline-5-sulfonylchloride 2-Methylindoline (10mlitre, 76.8mmol) was dissolved in 100mlitre of dichloromethane and then cooled down to 0C. To this solution were added pyridine (18.7mlitre, 0.22mol) and trifluoroacetic anhydride (24mlitre, 0.17mol). The reaction mixture was stirred at room temperature for 6 hours, diluted with 300mlitre of dichloromethane, and then washed twice with 150mlitre of 5% HCl. The dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated to obtain 15g of N-trifluoroacetyl-2-methyl-indoline. Yield: 85%

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONG WHA PHARMACEUTICAL INDUSTRIAL CO. LTD.; EP1021437; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 16800-68-3

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 21857-45-4, name is 5-Methoxyindoline, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methoxyindoline

0 degree celcius at the 5-methoxy indoline (257mg, 1.72mmol) and triethylamine (487ul, 3.44mmol) was added to dichloromethane (8.0mL), and then slowly added 4-methoxy-3- (4- (2,2,2-trichloro-acetyl) piperazin-1-yl) benzene-1-sulfonyl chloride (500mg, 1.15mmol). After 10 minutes the reaction temperature was raised to 25 , the reaction overnight. Was added 50mL of dichloromethane and then with saturated sodium chloride solution (40 mL), the organic phase after separation was dried over anhydrous sodium sulfate. Filtered, the filtrate was spin dry, purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 5/1) to give the title compound as a white solid (554mg, 87.9%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 21857-45-4.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Zhang, Wenhe; Jin, Chuanfei; Zhang, Yingjjun; Zhang, Ji; (50 pag.)CN105367474; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 112656-95-8, The chemical industry reduces the impact on the environment during synthesis 112656-95-8, name is 7-Nitroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of DHEA (0.5 mmol, 1.0 eq) and isatin derivative(0.75 mmol, 1.5 eq) in EtOH (10 mL) was added Al2O3/KF (0.5 mmol,1.0 eq), the resulting mixture was stirred at reflux temperature for 6 h.Upon completion of the reaction indicated by the TLC, the mixture wasfiltered and the solid was washed with dichloromethane (DCM) forseveral times. The filtrate was then evaporated under vacuum, followedby addition of DCM and H2O. The mixture was then acidified with 4MHCl (pH=1-2). The aqueous layer was washed with DCM for severaltimes. The combined organic layers were then dried over Na2SO4 andevaporated under vacuum to the crude product, which was then subjectedto column chromatography, affording the corresponding product.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Yan-Tao; Du, Shuzhang; Wang, Song; Jia, Xuedong; Wang, Xiaojuan; Zhang, Xiaojian; Steroids; vol. 151; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem