Tag: M.W=100-200

Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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. Quality Control of 5-Nitroindoline-2,3-dione

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 611-09-6, its application will become more common.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 341988-36-1, name is Methyl indoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 341988-36-1

Example 1: Synthesis and analytical data of l-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro- indole-6-carboxylic acid methyl esterl-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro-indole-6-carboxylic acid methyl ester was synthesized starting from commercial available indoline-6-carboxylic acid methylester following the general procedure A using commercial available 4-ethoxy-benzene sulfonylchloride. ESI+, m/z+l=362, found; IH-NMR (CDCl3): delta(ppm)=8.25 (s, IH), 7.8.-7.65 (m, 3H), 7.15 (d, J=2Hz; 1H); 6.90 (d; J=3Hz; 2H), 4,10-3=90 (m, 7H), 2,95 (t, J=2Hz, 2H), 1.40 (t, J=2Hz, 3H) General procedure A: Coupling of sulfonic acid chlorides to indolines0.5 mmol of the Indoline were dissolved in a mixture of 2.5 mL dry dichloromethane and 0.5 mL dry pyridine under a nitrogen atmosphere. 0.6 mmol of the sulfonic acid chloride were added. The mixture was stirred at room temperature in a sealed tube for 6.5 h. Thereafter solvent was evaporated under vacuum. The crude product was purified by preparative HPLC-MS to give the corresponding sulfonamide.

The synthetic route of 341988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; ELARA PHARMACEUTICALS GMBH; JANSSEN, Bernd; AMMENN, Jochen; MUeLBAIER, Marcel; ALONSO, Jorge; WO2010/17827; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 60434-13-1, COA of Formula: C9H6ClNO2

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, 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. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, 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.

General procedure: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxoindoline-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H11NO

To a mixture of 3,3-dimethyloxindole 41 (50 mg, 0.31mmol, 1.00 equiv) and Cs2CO3 (202 mg, 0.62 mmol, 2.00 equiv) in THF (1.60 mL)was added p-nitrobenzyl bromide (101 mg, 0.47 mmol, 1.50 equiv). The reactionmixture was stirred overnight. Then, the reaction mixture was extracted with EtOAc(3 x 3 mL) and washed with brine. The combined organic phases were dried overMgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?4-nitrobenzyl-3,3-dimethyloxindole 3c (77.5 mg, 84percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.18 (d, J = 8.8 Hz,2H), 7.43 (d, J = 10.0 Hz, 2H), 7.25 (ddd, J = 7.3, 1.5, 0.7 Hz, 1H), 7.16 (td, J = 7.7,1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.1 Hz, 1H), 6.65 (dt, J = 7.7, 0.7 Hz, 1H), 5.01 (s, 2H),1.45 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.6, 147.6, 143.7, 141.1, 135.8, 128.0,127.9, 124.2, 123.2, 122.8, 108.7, 77.2, 44.4, 43.1, 24.7; IR (Neat Film NaCl) 2968,1707, 1613, 1522, 1343, 1173, 1111, 1009, 760; HRMS (MM: ESI-APCI+) m/zcalc?d for C17H17N2O3 [M+H]+ : 297.1234; found: 297.1239.

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:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its 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. HPLC of Formula: C10H9NO3

(i) Preparation of Ethyl-4-(2-phthalimidoethoxy)acetoacetate STR141 To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0 under nitrogen was added B 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.

The synthetic route of 2-(2-Hydroxyethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4572908; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to a cooled (0 C) solution of Ph3P (9.44 g, 36 mmol) in dry THF (60 mL), diisopropylazodicarboxylate (DIAD) (7.08 mL, 36 mmol) was added dropwise at stirring. The suspension obtained was stirred for 30 min and then a suspension of calixarene 9 (1:1 p-xylene complex, 6.40 g, 6 mmol) and 2-hydroxyethylpthalimide (6.88 g, 36 mmol) in THF (200 mL) was added dropwise. The stirring was continued for 1 h at low temperature and then for 24 h at room temperature. The reaction mixture (clear solution) was concentrated in vacuo to an oil, which was triturated with methanol. The solid formed was separated, washed with methanol and dried. Yield 89% (6.98 g, white powder). Mp 234-236 C (decomp.). 1H NMR (400 MHz, CDCl3) delta 7.93 (4H, m, ArHPht), 7.70 (4H, m, ArHPht), 6.96 (4H, s, ArH), 6.67 (4H, s, ArH), 6.65 (2H, s, OH), 4.44 (4H, t, J=6.6 Hz, NCH2), 4.24 (4H, t, J=6.6 Hz, OCH2), 4.18 (4H, d, J=2.9 Hz, ArCH2Ar), 3.25 (4H, d, J=12.9 Hz, ArCH2Ar), 2.10-1.35 (60H, m, HAd). 13C NMR (100 MHz, CDCl3) delta 168.10 (CO), 150.47, 149.01, 146.87, 141.49 (CAr), 133.83 (CHAr,Pht), 132.13, 132.09 (CAr), 127.72 (CAr,Pht), 124.96, 124.26 (CHAr), 123.22 (CHAr,Pht), 71.79 (OCH2), 43.70, 42.74 (CAd), 37.47 (NCH2), 36.91, 36.61 (CAd), 35.29, 35.26 (CAd), 31.11 (ArCH2Ar), 29.08, 28.76 (CHAd). FD-MS: m/z 1308.5 [M+H]+; C88H94N2O8·H (1308.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Vatsouro, Ivan; Serebryannikova, Alina; Wang, Leyong; Hubscher-Bruder, Veronique; Shokova, Elvira; Bolte, Michael; Arnaud-Neu, Franoise; Boehmer, Volker; Kovalev, Vladimir; Tetrahedron; vol. 67; 42; (2011); p. 8092 – 8101;,
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. 16800-68-3, name is 1-Acetylindolin-3-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

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:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6341-92-0, name is 6-Chloroisatin, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 6341-92-0

EXAMPLE 14a rac-6-Chloro-3-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one 4-Bromo-1-methyl-1H-pyrazole was prepared according to the procedure of Dusza, J. P. et al., U.S. Pat. No. 6,511,974 B1, published Jan. 28, 2003. To a solution of 4-bromo-1-methyl-1H-pyrazole (0.98 g, 6.0 mmol) in tetrahydrofuran (10 mL) at -78 C. was added n-butyllithium (2.5 M in hexanes, 2.76 mL, 6.90 mmol) (Aldrich) dropwisely. The mixture was stirred at -78 C. for 10 minutes. To the obtained brownish solution was added a solution of 6-chloroisatin (0.5 g, 2.76 mmol) (Crescent) in tetrahydrofuran (5 mL). The reaction mixture was warmed up to room temperature and stirred at room temperature for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate:dichloromethane, 1:1 V/V) to give rac-6-chloro-3-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one as a yellow solid. (Yield 0.22 g, 30%).

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7477-63-6, SDS of cas: 7477-63-6

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

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-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem