Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-1,3-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 7147-90-2, Quality Control of 5-Chloroisoindoline-1,3-dione

4- Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by /V-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide /V-[(5-chloro-l,3-dioxo-2-isondolinyl)methyl]- /V-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSOcI6): delta (ppm) = 4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J = 9.1 Hz, 2H), 7.22 (d, J = 9.1 Hz, 2H), 7.90 (d, J = 1.2 Hz, 2H), 7.97 (t, J = 1.2 Hz, IH), 12.71 (br s, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 51.77 (CH2), 54.72 (CH2), 114.39 (2 CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2 CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO). MS ( + ESI): m/z = 379 (M + H).

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, 5-Chloroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, Safety of 4-Chloroindoline

1 , 1 -dime th yleth yl 4-chloro-2, 3-dih ydro- 1 H-indole- 1 -carboxylateA solution of 4-chloro-2,3-dihydro-1 H-indole (4.0 g, 26.0 mmol), Boc20 (6.05 mL, 26.0 mmol), DIEA (9.10 mL, 52.1 mmol), DMAP (0.318 g, 2.60 mmol) was stirred at room temperature overnight. LCMS indicated complete conversion. The reaction mixture was poured into 0.1 N HCI (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to afford 1 ,1 – dimethylethyl 4-chloro-2,3-dihydro-1 H-indole-1 -carboxylate (6.36 g) as a yellow oily semisolid. LC-MS(ES) m/z = 198 [M+H-t-Bu]+. 1H NMR (400 MHz, DMSO-d6) delta ppm 1 .51 (s, 9 H), 3.07 (t, J=8.72 Hz, 2 H), 3.95 (t, J=8.72 Hz, 2 H), 6.98 (d, J=8.84 Hz, 1 H), 7.19 (t, J=8.08 Hz, 1 H), 7.48 – 7.70 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3339-73-9, A common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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.

To a solution of 3-(1,3-dioxoisoindolin-2-yl)propanoic acid (256 mg, 1.17 mmol) in CH2Cl2 (5.9mL) were added (COCl)2 (200 L, 2.33 mmol) and DMF (1 drop) at 0 C.The reaction mixture was stirred at 0 C for 30 min and at room temperature for 3 h. Thesolvents were removed under reduced pressure. Azeotropic distillations were carried out withtoluene (2 × 3 mL) under reduced pressure. The residue (acid chloride) was used for next stepwithout further purification

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Natori, Yoshihiro; Hwang, Candy S.; Lin, Lucy; Smith, Lauren C.; Zhou, Bin; Janda, Kim D.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1020 – 1031;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5332-26-3 as follows. Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

To a solution of benzyl 2-phenylacetate (1 1.3 g, 50 mmol) in dry THF (100 mL) at -78 C under nitrogen was added LiHMDS (2.5 M in THF, 40 mL, 100 mmol) dropwise over 25 min. A solution of 2-(bromomethyl)isoindoline-1,3-dione (14.4 g, 60 mmol) in THF (100 mL) was then added dropwise and the mixture was stirred at -78 C for 2 h, then allowed to warm to r.t. and stirred overnight. The mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (DCM/MeOH = 100:0- 100:1) to give the desired product (12.5 g, 65% yield) as a white solid. LCMS (ES-API): Rt 2.78 min; m/z 386.1 [M+H]+.

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 40314-06-5, The chemical industry reduces the impact on the environment during synthesis 40314-06-5, name is 5-Methylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Isolation and analytic data for 13, observed in the crossover study, was obtained by independent preparation using the following procedure. Isovaleryl chloride (65 muL, 0.53 mmol) was added to a mixture of 4-methylphthalimide (200 mg, 1.2 mmol), isobutyraldehyde (108 muL, 1.19 mmol), NaI (170 mg, 1.1 mmol), 4 A MS (100 mg), triethylamine (150 muL, 1.1 mmol), ethyl acetate (1.1 mL), and acetonitrile (1.1 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with 1 M NaOH (3×) and brine. The organic phase was dried (MgSO4) and concentrated. Purification by flash chromatography (SiO2, hexanes:EtOAc 4:1) gave 13 (105 mg, 0.33 mmol, 62%) as a white solid. 1H NMR (300 MHz, CDCl3): delta 7.76 (d, J=7.6Hz, 1H), 7.68 (s, 1H), 7.55 (d, J=7.6Hz, 1H), 6.19 (d, J=10.4Hz, 1H), 2.90 (nfom, 1H), 2.52 (s, 3H), 2.23 (d, J=7.3Hz, 2H), 2.09 (septet, J=6.7Hz, 1H), 1.08 (d, J=6.6Hz, 3H), 0.91 (d, J=6.6Hz, 3H), 0.90 (d, J=7Hz, 3H), and 0.88 (d, J=7.6Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 171.9, 167.1, 166.9, 145.8, 135.0, 131.8, 128.9, 124.2, 123.6, 79.1, 43.1, 29.5, 25.6, 22.3, 22.1, 19.0, and 17.9. IR (neat): 2963, 2875, 1779, 1748, 1721, 1618, 1468, 1430, 1363, 1101, and 1006 cm-1. HRMS (ESI-TOF): Calcd for C18H23NNaO4+ [M+Na+] requires 340.1519; found 340.1522. Mp: 53-55 C.

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, 5-Methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4.92 g (30 mmol) of 5-nitroindoline is introduced by portions into a 250 ml double-necked flask, under argon atmosphere, containing a suspension of 2.4 g (60 mmol) of NaH (60%) in 60 ml DMF,. The vigorous hydrogen evolution is accompanied by the formation of a red suspension. Agitation is maintained for 30 minutes at 23 C. before the addition, by portions, of 4.74 g (30 mmol) of 3-dimethylaminopropyl chloride hydrochloride. The reaction mixture is agitated and heated at 60 C. during 18 hours. The whole is finally poured into 200 ml of a water/ice mixture. The product is then extracted twice with 100 ml of AcOEt. The organic solution is washed successively with 100 ml of water and 100 ml of brine. After drying over MgSO4 and concentration under vacuum, the evaporation residue is purified by flash chromatography an a silica column (eluent: AcOEt/MeOH 100/0 to 0/100). A dark yellow oil is obtained with a yield of 48%.

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

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6653312; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 26; Compound of Formula VII, Wherein R1 and R2 Taken Together with the Carbon Atom to which they are Attached are CCH2, and R20=(4-Pyridin-3-yl-1H-triazol-1-ylbutyl), Rx=Ac; Step 26a.; To a solution of commercially available 2-(4-bromo-butyl)-isoindole-1,3-dione (7.1 mmol) in DMF (7 ml) was added sodium azide (5 eq.). After stirring at room temperature overnight, the mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed 3 times with water, once with brine, dried over MgSO4, filtered and concentrated under vacuum to give the desired azide product in quantitative yield. 13C NMR (CDCl3, ppm) delta: 168.4, 134.0, 132.1, 123.3, 50.9, 37.3, 26.3, 26.3, 25.9.

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, 2-(4-Bromobutyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Or, Yat Sun; Tang, Datong; Gai, Yonghua; Sun, Ying; Xu, Guoyou; Wang, Zhe; US2006/122128; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

To solution of oxindole (4.43 g, 33.3 mmol) in AcOH (35 mL) was added NIS (9 g, 40.0 mmol) at rt. The mixture was stirred for 1.5 hours at which point water (60 mL) was slowly added dropwise, followed by about 5 mL of EtOAc to solubilize impurities. The solid was filtered, washed with a small amount of EtOAc followed by diethyl ether, to give 5-iodo-oxindole (5.4 g, 62%) as a light pink solid clean by proton NMR in DMSO.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. Recommanded Product: 5-Bromoisoindolin-1-one

A solution of 5-bromoisoindolin-l-one (10 g, 47.16 mmol) in dioxane (450 mL) was degassed before Xantphos (2.73 g, 4.72 mmol), DIPEA (9.88 mL, 56.59 mmol), Pd2(dba)3 (2.159 g, 2.36 mmol) and methyl 3-mercaptopropanoate (32.6 mL, 330.12 mmol) wasadded. The reaction was heated to 80 C for lh. The reaction was concentrated in vacuo. Approximately half of the material was purified by flash chromatography eluting with 0- 5% methanol in EtOAc to afford 4.69g of product. Only half the material was purified this way because the crude material solidified part way through loading onto the column. The solidified material was triturated with methanol and 4.48 g of product was collected byfiltration as a colorless solid. The mother liquor was concentrated in vacuo and purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 1. lg product. This was combined with the material from the first column to give l0.27g (86%) of the title compound.LC/MS: m/zrr252 [M+H]. ?H NMR (500 MHz, DMSO-d6) i5 2.69 (t, 2H), 3.26 (t, 2H),3.60 (s, 3H), 4.34 (s, 2H), 7.38 (d, 1H), 7.52 (s, 1H), 7.58 (d, 1H), 8.48 (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 552330-86-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; LEVER, Sarah; NARJES, Frank; OLSSON, Roine, Ingemar; VON BERG, Stefan; (124 pag.)WO2018/229155; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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: 39603-24-2

General procedure: To a mixture of isatin(s)/acenaphthoquinone/cyclic ketone(s) (1 mmol) and anthranilamide (1mmol) in ethanol(96%, 2 mL), sulfamic acid (0.2 mmol) was added. Thereaction mixture was stirred at ambient temperature forthe time mentioned in table 2 until completion of reaction,as monitored by TLC. After the completion ofreaction, the precipitated products was just filtered. Theconfirmation of isolated products was done by spectraltechniques such as 1H, 13C NMR, IR and massspectrometry.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mane, Mansing M.; Pore, Dattaprasad M.; Journal of Chemical Sciences; vol. 128; 4; (2016); p. 657 – 662;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem