Synthesis of indole derivatives. I. 2-Phenylindole-3-acetic acid from quinoline was written by Ochiai, Eiji;Tamai, Yoshikazu. And the article was included in Itsuu Kenkyusho Nempo in 1963.Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid This article mentions the following:
Into a solution of 4.88 g. 4-quinolyl(phenyl)acetonitrile in 15 cc. AcOH is introduced 3.8 cc. 33% H2O2, and the mixture heated 3 hrs., at 70掳 concentrated in vacuo, and extracted with CHCl3 to give 3.65 g. 4-benzoylquinoline 1-oxide (I), m. 15-7掳 (decomposition). To a solution of 2.49 g. I in 30 cc. CHCl3 is added a solution of 2.0 g. tosyl chloride in 20 cc. CHCl3, the mixture heated 10 min., 20 cc. 8% NaOH added, and the mixture agitated 40 min. to give 2.1 g. 4-benzoylcarbostyril (II), needles, m. 263掳. A solution of 4 g. II in 80 cc. AcOH is subjected to catalytic reduction with 1 g. 40% Pd-C to give 3.1 g. 4-(伪-hydroxybenzyl)carbostyril, needles, H m. 251掳 (Me2CO), and 0.2 g. 4-benzylcarbostyril (III), needles, m. 271掳 (MeOH). Catalytic reduction of 12 g. H by the use of Raney Ni under high pressure at 120掳 in MeOH gives two isomers of 4-(伪-hydroxybenzyl)-3,4-dihydrocarbostyril (IV), m. 183掳 (needles from MeOH), and m. 179掳 (needles from MeOH), as well as 0.2 g. 4-benzyl-3,4-dihydrocarbostyril (V), needles, m. 163掳 (MeOH). Catalytic reduction of III using Raney Ni under high pressure gives V. To a solution of 732 mg. CrO3 in 5 cc. H2O and 50 cc. AcOH is added a solution of 2.53 g. IV in 40 cc. AcOH, and the mixture heated 30 min. at 80掳 to give 2.04 g. 4-benzoyl-3,4dihydrocarbostyril (VI), prisms, m. 230掳 (MeOH);’ monoxime m. 165掳 (decomposition). VI (2.51 g.) is added to 40 g. EtOH containing 10 g. dry HCl gas and the mixture refluxed 25 hrs. to give 1.92 g. Et 2-phenylindole-3-acetate (VII), b0.001 180-5掳. Reduction of 2.79 g. VII with LiAlH4 in tetrahydrofuran solution gives 1.71 g. 2-phenyl3-(尾-hydroxyethyl)indole, needles, m. 144-6掳 (C6H6-ligroine). Heating 1.40 g. VII with 20% ethanolic HCl solution under refluxing gives 1.0 g. 2-phenylindole-3-acetic acid, leaves, m. 179掳 (C6H6). In the experiment, the researchers used many compounds, for example, 2-(2-Phenyl-1H-indol-3-yl)acetic acid (cas: 4662-03-7Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid).
2-(2-Phenyl-1H-indol-3-yl)acetic acid (cas: 4662-03-7) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles