Category: 104618-32-8

Electric Literature of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

4-Cyanophenyl hydrazine hydrochloride (4.41 g, 0.026 mole) was dissolved in acetic acid (100 ml) and sodium acetate (2 g) was added. 4-Phthalimido cyclohexanone (6.4 g, 0.026 mole) was added and the mixture heated under reflux overnight. The solvent was removed in vacuo and the residue triturated with methanol to give 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole as a beige solid, (5.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;; ; Patent; Smithkline Beecham plc; US5827871; (1998); A;; ; Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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. COA of Formula: C14H13NO3

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 104618-32-8, 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 104618-32-8 as follows.

A solution of N-(4-oxocyclohexyl)phthalimide (14, 5.00 g, 21 mmol, 1 eq.) and 4-methoxyphenylhydrazine hydrochloride (3.59 g, 21 mmol, 1 eq.) in dry ethanol (100 mL) was heated at reflux for 2.5 h. After cooling down to room temperature, the precipitate was filtrated off and washed with ethanol 96% (3 * 10 mL). The solid was dried under reduced pressure and freeze-dried overnight. Rf = 0.66 (cyclohexane/ethyl acetate/dimethylethylamine 5:5:0.2). Colorless solid, mp 222-223 C, yield 6.88 g (97%). Purity (HPLC): 84.1% (tR = 22.2 min). C21H18N2O3 (346.4 g/mol). Exact mass (APCI): m/z = 347.1389 (calcd. 347.1390 for C21H19N2O3 [M + H+]). 1H NMR (400 MHz, DMSO-D6): delta (ppm) = 2.03-2.11 (m, 1H, 2-H), 2.67 (tt, J = 12.3/6.4 Hz, 1H, 2-H), 2.80-2.98 (m, 3H, 1-CH2, 4-H), 3.20-3.28 (m, 1H, 4-H), 3.71 (s, 3H, OCH3), 4.43-4.52 (m, 1H, 3-H), 6.65 (dd, J = 8.7/2.4 Hz, 1H, 7-H), 6.82 (d, J = 2.4 Hz, 1H, 5-H), 7.15 (d, J = 8.7 Hz, 1H, 8-H), 7.84-7.91 (m, 4H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 10.61 (s, 1H, NH). 13C NMR (101 MHz, DMSO-D6): delta (ppm) = 22.6 (1C, C-1), 24.7 (1C, C-4), 26.5 (1C, C-2), 47.8 (1C, C-3), 55.3 (1C, OCH3), 99.7 (1C, C-5), 106.3 (1C, C-4a), 109.9 (1C, C-7), 111.2 (1C, C-8), 123.0 (2C, C-4phth, C-7phth), 127.2 (1C, C-4b), 131.3 (1C, C-8a), 131.5 (2C, C-3aphth, C-7aphth), 134.2 (1C, C-9a), 134.4 (2C, C-5phth, C-6phth), 153.0 (1C, C-6), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3425 (w, N-H), 3379 (w, C-H, arom), 2924 (w, C-H, aliph), 1697 (s, C=O), 1597 (w, C-C, arom).

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference of 104618-32-8, 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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Example 14 3-Amino-6-n-butyloxy-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (1.12 g) with 4-n-butyloxyphenyl hydrazine hydrochloride (1.00 g) and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.47 g), mp 227 – 229C.

The chemical industry reduces the impact on the environment during synthesis 2-(4-Oxocyclohexyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of N-(4-oxocyclohexyl)phthalimide (14, 3.53 g, 15 mmol, 1 eq.) and 4-(methylsulfonyl)phenylhydrazine (2.70 g, 15 mmol, 1 eq.) in glacial acetic acid (110 mL) was heated at reflux for 47 h. The mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (200 mL). Afterwards, the organic layer was washed with water (2 * 70 mL) and brine (70 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by fc with a gradient (? = 6 cm, l = 13 cm, v = 60 mL, cyclohexane/CH2Cl2 60:40, 50:50, 30:70, 0:100, CH2Cl2/methanol 100:10, Rf = 0.51 (cyclohexane/ethyl acetate/formic acid 3:7:0.2)). Pale yellow solid, mp 282-284 C, yield 4.50 g (79%). Purity (HPLC): 86.6% (tR = 19.6 min). C21H18N2O4S (394.5 g/mol). Exact mass (APCI): m/z = 395.1072 (calcd. 395.1060 for C21H19N2O4S [M + H+]). 1H NMR (600 MHz, DMSO-D6): delta (ppm) = 2.11 (d, J = 12.3 Hz, 1H, 2-H), 2.64-2.74 (m, 1H, 2-H), 2.92-3.01 (m, 3H, 1-CH2, 4-H), 3.12 (s, 3H, CH3), 3.29-3.33 (m, 1H, 4-H), 4.47-4.54 (m, 1H, 3-H), 7.49 (d, J = 8.6 Hz, 1H, 8-H), 7.56 (dd, J = 8.6/1.4 Hz, 1H, 7-H), 7.84-7.93 (m, 5H, 5-H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 11.45 (s, 1H, NH). 13C NMR (151 MHz, DMSO-D6): delta (ppm) = 22.5 (1C, C-1), 24.2 (1C, C-4), 26.2 (1C, C-2), 44.6 (1C, CH3), 47.4 (1C, C-3), 108.3 (1C, C-4a), 111.2 (1C, C-8), 117.3 (1C, C-5), 118.9 (1C, C-7), 123.0 (2C, C-4phth, C-7phth), 126.3 (1C, C-4b), 130.7 (1C, C-6), 131.5 (2C, C-3aphth, C-7aphth), 134.5 (2C, C-5phth, C-6phth), 136.8 (1C, C-9a), 138.5 (1C, C-8a), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3348 (m, N-H), 2939 (w, C-H, aliph), 1697 (s, C=O), 1620 (w, C-C, arom), 1130 (s, SO2).

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 104618-32-8.

Reference:
Article; Heimann, Dominik; Boergel, Frederik; de Vries, Henk; Bachmann, Kim; Rose, Victoria E.; Frehland, Bastian; Schepmann, Dirk; Heitman, Laura H.; Wuensch, Bernhard; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1436 – 1447;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 104618-32-8, 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. 104618-32-8 name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 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 14 3-Amino-6-n-butyloxy-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (1.12 g) with 4-n-butyloxyphenyl hydrazine hydrochloride (1.00 g) and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.47 g), mp 227-229 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-32-8, 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 104618-32-8 as follows.

To a solution of the title compound from above step A (1.5 g, 6.7 mmol) in ethanol (100 mL) was added ketone derivative (1.6 g, 6.7 mmol) in ethanol (50 mL). The reaction mixture was stirred for 5 h at room temperature. The solvent was removed to give the title compound as a solid (3.1, quantitative). The product was used in the next step without any purification.

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 104618-32-8, These common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)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.

Example 8 3-Amino-6-methoxycarbonyl-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (0.37 g) with 4-ethoxycarbonylphenylhydrazine hydrochloride (0.33 g), and subsequent deprotection by the method described in example 3, gave the title compound free base. This was converted to the oxalate salt (0.11 g), mp 230-240C dec.

The synthetic route of 104618-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

(B) 15gm (0.0617mole) 4-phthalimido cyclohexanone was dissolve in 150ml Ethylacetate. Cool the mass to 0C. Add Br2 solution (9.8gm Bra in 25ml of methanol) and0.25gm of Aids under stirring. Stop stirring and allow initiating bromination and findingclear solution then add remaining quantity of Br2 solution and stir for 10-15mins. Washthe reaction mass with 75ml 2% NaS2O3 solution then wash organic phase with 75ml8%NaHCO3. Then in last wash it with brine solution. Collect organic masses andevaporate it under vacuum. Dry it at 50C for 2-3hrs.YIELD: 15gms(75.2%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem