Month: May 2021

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. 251085-87-7, name is Methyl 5-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 5-bromo-2-chlorobenzoate

5-Bromo-2-chlorobenzaldehyde (74c). A solution of pyrrolidine (4.00 g, 56.0 mmol) in MTBE (12 mL) was added dropwise over 20 min to a solution of Red-Al (3.4 M solution in toluene, 16 ml, 54.4 mmol) in MTBE (33 mL) maintained at -20 C. The mixture was stirred for 1 h at 25 C. A solution of potassium tert-butoxide (0.60 g, 5.36 mmol) in THF (3 mL) was added. The resulting solution was added dropwise to a solution of 2-chloro-5-bromobenzoic acid methyl ester (72, 6.80 g, 27.3 mmol) in MTBE (15 mL) at 10 C. After 15 min the mixture was quenched with 2 N HCl (300 mL). Repeated recystallizations (hexanes) of the recovered material gave a crude solid (3.22 g, 54%, mp 43-46 C), which was used without further purification in the next step.; The synthesis of benzaldehyde chlorooxime synthons 52 is depicted in Scheme 4, below. Of the eight aldehydes 44e-f and 74a-f, only 44e and 74d were commercially available. The preparation of aldehyde 44f began with the known three-step transformation of 4-methyl-3-nitrobenzonitrile 63 to methoxy compound 64. See Reiner, J. E., et al., Bioorg. Med. Chem. Lett., 12, 1203-1208 (2002). alpha-Bromination of 64 using one equivalent of N-bromosuccinimide gave little selectivity between the mono- and dibromo adducts, but the analogous reaction using 2.5 equivalents gave dibromide 65 almost exclusively. Silver nitrate oxidation of dibromide 65 gave aldehyde 44f. See Hill. R. A., et al., J. Chem. Soc., Perkin Trans., 1, 2209-2215 (1987). The reaction of the o-nitrotoluene 63 with N,N-dimethylformamide dimethyl acetal in DMF gave the enamine 66, which underwent oxidative cleavage using sodium periodate in THF, see Riesgo, E. C., et al., J. Org. Chem., 61, 3017-3022 (1996), to give aldehyde 74a via a more facile preparation than previously reported. See Dann, O., et al., Liebigs Ann. Chem., 3, 409-425 (1984). Aldehyde 74b also has been prepared previously. See Schultz, E. M., et al., J. Med. Chem., 19(6), 783-787 (1976). A more expedient preparation of 74b began with chlorotoluene 67 undergoing alpha-bromination to 68, see Gilbert, A. M., et al., J. Med. Chem., 43, 1203-1214 (2000), by a modification of the original procedure. See Liu, P., et al., Synthesis, 14, 2078-2080 (2001). The reaction of 68 with 2-nitropropane and sodium ethoxide in ethanol gave 74b. See Mallory, F. M., et al., Tetrahedron, 57, 3715-3724 (2001). Commercially available aldehyde 69 and aldehyde 71, see Hino, K., et al., Chem. Pharm. Bull., 36(6), 3462-3467 (1988), which had been prepared via a Sandmeyer reaction from commercially available 70, were converted to methyl esters 72 and 73, respectively. The esters were converted to aldehydes 74c and 74e, respectively, using Red-Al(sodium bis(2-methoxyethoxy)aluminium hydride) (Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, United States of America), pyrrolidine, and potassium tert-butoxide in methyl tert-butyl ether. See Abe, T., et al., Tetrahedron, 57, 2701-2710 (2001). Cyanoaldehyde 74f was prepared by debromocyanation of 44d. See Laali, K. K., et al., J. Org. Chem., 58, 1385-1392 (1993). Aldehydes 44e-44f and 74a-74f were converted to oxime derivatives 75a-h (of which 75a,e were known previously), see Quan, M. L., et al., J. Med. Chem., 42(15), 2752-2759 (1999), using hydroxylamine hydrochloride in either water/ethanol or pyridine/ethanol. The oximes were treated with N-chlorosuccinimide in DMF to give chlorooximes 52a-h, following the procedure reported for 52e. See Liu. K.-C., et al., J. Org. Chem., 45, 3916-3918 (1980). The chlorooximes 52 were reacted with acetylenes 51 without further purification.; Reagents and conditions: (a) H2, 10% Pd/C, EtOH; (b) NaNO2, aq. H2SO4; (c) CH3l, NaH, DMF; (d) NBS, benzoyl peroxide, CCl4; (e) AgNO3, aq. EtOH; (f) DMFDMA, DMF; (g) NalO4; aq. THF; (h) diethyl phosphite, (i-Pr)2NEt, THF; (j) 2-nitropropane, NaOEt, EtOH; (k) NaNO2, aq. HCl, then CuCN, KCN; (I) MeOH, H2SO4; (m) DCC, DMAP, MeOH, CH2Cl2; (n) Red-Al, t-BuOK, pyrrolidine, MTBE; (o) NH2OH HCl, H2O/EtOH or Py/EtOH (p) NCS, DMF.

The synthetic route of 251085-87-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EP1719767; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6836-21-1, 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. 6836-21-1 name is Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, 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.

150 ml of ethanol is loaded into a three-necked reaction flask, magnetically stirred and equipped with a temperature probe, and cooled to 5C. When the temperature of 5C has been reached, 11.3 g of powdered calcium chloride(0.102 mol) is added, followed by 8.2 g of sodium borohydride (0.217 moles). After a few minute stirring at 5C, 10 g of 2-(7-methoxynaphthalen-1-yl)acetic acid ethyl ester 4 (41 mmols), dissolved in 100 ml of anhydrous THF, is added, the temperature being maintained under 10C. At the end of the addition the temperature is increased to room temperature and maintained at that temperature for about 2 hours. 5 ml of water is added slowly at the end of the reaction. 40 ml oftoluene and 20 ml of 30% HCl are then added. The phases are separated by re-extracting the aqueous phase with 20ml of toluene. The combined organic phases are washed with 40 ml of water, and then concentrated under vacuum to dryness to obtain 8.0 g of 2-(7-methoxynaphthalen-1-yl)ethanol 12. Yield 97%. The intermediate obtained was identifiedby NMR analysis: 1H NMR (400 MHz, DMSO-d6) delta 7.83 (d, 2H), 7.70 (m, 1H), 7.36 (m, 2H), 7.27 (m, 1H), 7.18 (m, 1H),3.92 (s, 3H), 3.75 (t, 2H), 3.29 (s, 1H), 3.19 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Procos S.p.A.; Barozza, Alessandro; Veronese, Martino; Roletto, Jacopo; Paissoni, Paolo; EP2703383; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1462-12-0, name is Diethyl 2-ethylidenemalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H14O4

Synthesis of compound 9.4. To a solution of compound 9.3 (1.3g, 4.86mmol, 1.0 equiv) and diethyl 2-ethylidenemalonate (0.9 g, 4.86mmol, 1.0 equiv) in ethanol (13 mL) was added sodium ethoxide (0.59g, 8.74mmol, 1.8 equiv) at room temperature. The mixture was refluxed for 3 hours then the solvent was removed under reduced pressure. The crude material was purified via flash column chromatography to yield compound 9.4 (2.6g, 65%>). MS (ES): m/z 409 [M+H]+.

The synthetic route of 1462-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 87661-20-9 as follows. Formula: C8H14O2

Example 73 (2S)-1-({1-[2-(2-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60 starting from 4-chloromethyl-5-methyl-2-(2-chloro-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. Steps A] and C] were performed as outlined in example 60, step B] was done according to example 69. The title compound was obtained as a light brown gum. MS (ISP): 399.3 (MH+) and 401.4 (MH+).

According to the analysis of related databases, 87661-20-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 204707-42-6, name is Methyl 4-fluoro-2-methoxybenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H9FO3

Step 2: Combine the product of Step 1 (1.43 g, 7.2 mmol) and iron powder (0.018 g) in CH2Cl2 (15 ml ). Add dropwise Br2 (0.44 ml, 8.7 mmol) in CH2Cl2 (5 ml). Stir 18 h and wash with water, then 1N NaOH. Dry (MgSO4) and concentrate to obtain the bromide 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; Schering Corporation; US2004/220194; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 6065-54-9, 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. 6065-54-9, name is Dimethyl 2,2-dimethylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. 2,2-Dimethyl-3-oxo-3-(pentylamino)propionic acid Following the procedure of Example 1A and B except substituting dimethyl 2,2-dimethylmalonate for dimethyl malonate, the title compound is obtained.

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, Dimethyl 2,2-dimethylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4654356; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, 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. COA of Formula: C6H12O3

Starting material 209a (9.9 g, 75 mmol) was dissolved in THF (100 mL) and water (25 mL). LiOH (3.4 g, 80.9 mmol), the resulting mixture was stirred at room temperature overnight. 1 N HCl (100 mL) was added and extracted with EtOAc. The organic extracts were combined, washed with brine, dried (MgSO4) to give compound 209b (8.8 g, 93%).

The synthetic route of Methyl 4-methoxybutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2006/264489; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1732-08-7, name is Dimethyl pimelate, belongs to esters-buliding-blocks 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 1732-08-7, Application In Synthesis of Dimethyl pimelate

Dimethyl pimelate (3.76 g, 20 mmol) was added dropwise to a suspension of NaH(1.06g, 26.6 mmol, 60% in mineral oil) in dry THF (20 mL). The resulting slurry wasstirred at RT overnight. The reaction was quenched with water (5 mL), extracted withEtOAc (20 mL× 3), washed with brine, dried (Na2SO4), and concentrated undervaccum. The residue was chromatographed with petrolum ether-EtOAc (20:1) to give the desired methyl 2-cyclohexanonecarboxylate as a colorless oil. (2.42 g, 77%).

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:
Article; Qian, Hua; Gu, Guoxian; Zhou, Qinghai; Lu, Jiaxiang; Chung, Lung Wa; Zhang, Xumu; Synlett; vol. 29; 1; (2018); p. 51 – 56;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 850449-93-3, name is Methyl 2-(5-amino-2-methylphenyl)acetate, molecular formula is C10H13NO2, 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: Methyl 2-(5-amino-2-methylphenyl)acetate

6-Chloro-4-phenylamino-pyridine-3-carbaldehyde 18 (21 mg, 0.09 mmol) is mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (18 mg, 0.1 mmol) and potassium carbonate (37 mg, 0.27 mmol) in DMF (2 mL). The mixture is heated to 100 0C for 16 h. After cooling to rt and removing solvent in vacuo, the crude product is purified using flash chromatography (hexane : ethyl acetate = 1 : 1). The title compound 3-(5-amino- 2-methyl-phenyl)-7-chloro-l-phenyl-lH-[l,6]naphthyridin-2-one 19 is obtained as a pale solid. 1H NMR (400MHz, CDCl3) delta 8.53 (s, IH), 7.68 (s, IH), 7.53-7.57 (m, 2H), 7.47 -7.51 (dt IH), 7.20-7.23 (m, 2H), 6.96 (d, IH), 6.59 (dd, IH), 6.58 (s, IH), 6.52 (s, IH), 2.05 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 850449-93-3, its application will become more common.

Reference:
Patent; IRM LLC; WO2008/51757; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1202-25-1, The chemical industry reduces the impact on the environment during synthesis 1202-25-1, name is Methyl 4-dimethylaminobenzoate, I believe this compound will play a more active role in future production and life.

PREPARATION 10i 1-(4-N,N-Dimethylaminophenyl)-1-methylethylamine Following a procedure similar to that described in Preparation 10a, but using methyl 4-N,N-dimethylaminobenzoate as a starting material, in a relative amount similar to that used in that Preparation, the title compound was obtained in a yield of 48%. Nuclear Magnetic Resonance Spectrum (CDCl3), delta ppm: 1.48 (6H, singlet); 1.70 (2H, broad singlet); 2.95 (6H, singlet); 6.65-6.80 (2H, multiplet); 7.30 (2H, doublet, J=9 Hz). Infrared Absorption Spectrum (liquid film), numax cm-1: 2960, 1615, 1525, 815.

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, Methyl 4-dimethylaminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sankyo Company, Limited; US5536714; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics