55150-24-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Benzoic acid, 5-methyl-2-(methylamino)-, methyl ester is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It plays a crucial role in the production of various drugs and pesticides, contributing to the development of new and effective treatments and protection methods.
Used in Flavor and Fragrance Industry:
Benzoic acid, 5-methyl-2-(methylamino)-, methyl ester is also used in the production of flavor and fragrance compounds. Its unique properties allow it to contribute to the creation of various scents and tastes, enhancing the sensory experience of different products.
Used as a Chemical Intermediate:
Benzoic acid, 5-methyl-2-(methylamino)-, methyl ester serves as a chemical intermediate for the synthesis of various other organic compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of a wide range of products.
Used in Organic Chemistry Research:
Furthermore, it has potential applications in the field of organic chemistry as a building block for the synthesis of complex molecules. Researchers can utilize Benzoic acid, 5-methyl-2-(methylamino)-, methyl ester to construct more intricate chemical structures, leading to advancements in material science and the discovery of new chemical entities.

InChI:InChI=1/C10H13NO2/c1-7-4-5-9(11-2)8(6-7)10(12)13-3/h4-6,11H,1-3H3

Upstream product

• 127117-54-8 N,4-dimethyl-2-methoxycarbonyl-N-(p-toluenesulfonyl)aniline 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 34161-82-5 2-methoxycarbonyl-4-methyl-N-(p-toluenesulfonyl)aniline 
• 18595-16-9 2-amino-5-methylbenzoic acid methyl ester 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 623-08-5 N-methyl-p-toluidine 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

A novel pathway for the thermolysis of N-nitrosoanthranilates using flash vacuum pyrolysis leading to 7-aminophthalides

Flash vacuum pyrolysis of methyl N-methyl-N-nitrosoanthranilate leads to elimination of nitric oxide and disproportionation of the formed N-radical to 7-(methylamino)phthalide and methyl N-methylanthranilate. This transformation was found to be a convenient, solvent-free method for the preparation of 7-(methylamino)phthalides. An alternative route through pyrolysis of N-benzyl-N-methyl anthranilates was also investigated. This journal is

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Palladium/copper-catalyzed aerobic oxidative C-H carbonylation for the synthesis of o-aminobenzoates

The palladium/copper-catalyzed aerobic oxidative C-H carbonylation for the synthesis of o-aminobenzoates is described. Molecular oxygen is used as the terminal oxidant. This methodology proceeds with a wide range of N-substituted anilines and alcohols and gives straightforward access to valuable o-aminobenzoates.

Synthesis and biological properties of 3-methyl-10-propargyl-5,8-dideazafolic acid

The synthesis of N3-methyl-10-propargyl-5,8-dideazafolic acid (1b) is described. Ring closure of methyl-5-methylanthranilate with chloroformamidine hydrochloride gave a high yield of pure 2-amino-4-hydroxy-6-methylquinazoline treatment of which with indomethane/sodium hydroxide provided the corresponding 3-methylquinazoline (6) which was converted to its 2-pivaloylamino derivative. This synthetic approach, next involving functionalisation of the 6-methyl group, was not further pursued because of difficulty encountered in removing the pivaloyl group. Methyl 5-methylanthranilate was treated with p-toluenesulfonyl chloride and the product then N-methylated. The tosyl group was cleaved with hydrogen bromide/phenol and the resulting methylamine ring-closed with chloroformamidine hydrochloride to provide 2-amino-1,4-dihydro-1,6-dimethyl-4-oxoquinazoline (11). The 2-pivaloylamino derivative of 11 was prone to hydrolytic deamination when attempts were made to remove the pivaloyl group and further elaboration of this heterocycle, with the intention of obtaining N1-methyl-10-propargyl-5,8-dideazafolic acid was, too, not attempted. Di-t-butyl N-(4-propargylamino)benzoyl)-L-glutamate was therefore prepared and coupled with 2-amino-6-bromomethyl-4-hydroxyquinazoline hydrobromide. The resulting antifolate diester was N-monomethylated. Removal of the t-butyl groups with trifluoracetic acid afforded the target compound 1b and its structure was proved by degradation to the quinazoline 6. Its IC50 for L1210 thymidylate synthase (TS) was 26 μM; the control value for 10-propargyl-5,8-dideazafolic acid (1a) was 0.02 μM. Thus the substitution of the lactam hydrogen in 1a by a methyl group reduced the TS inhibition by 1300-fold. Compound 1b was poorly cytotoxic to L1210 cells in culture (ID50 > 100 μM). An unperturbed lactam group in this class of antifolate is important for binding to TS.