Whalley, W. B. published an article in 1951, the title of the article was Organic fluoro compounds. V. ω-Trihaloacetophenones.HPLC of Formula: 65417-22-3 And the article contains the following content:
cf. C.A. 45, 9001b. 6,2,4-MeO(HO)2C6H2CO2Me (I) (2.2 g.), 0.7 g. Ac2O, and 15 mL. AcOH, saturated with BF3 and the precipitate crystallized from MeOH, give 2.2 g. Me 3-acetyl-2,4-dihydroxy-6-methoxybenzoate (II), m. 170°; II results also from 1.7 g. I, 10 mL. MeCN, 4 g. ZnCl2, and 2 g. AlCl3 in 100 mL. ether saturated with HCl at 5° and the ketimine salt hydrolyzed after 24 h. with H2O. Hydrolysis of II with KOH gives 4,2,6-MeO(HO)2C6H2Ac (III), m. 137°. 4,2,6-MeO(HO)2C6H2COCCl3 (2 g.), 0.7 g. Ac2O, and 5 mL. AcOH, saturated with BF3, give 2.2 g. 2,6-dihydroxy-4-methoxy-3-trichloroacetylacetophenone (IV), fawn, m. 115°; hydrolysis with aqueous KOH gives III; 0.5 g. IV in 7 mL. MeOH containing 1 drop 60% KOH, refluxed 5 min., gives a quant. yield of II; warmed with 2 N NaHCO3, IV gives 3-acetyl-2,4-dihydroxy-6-methoxybenzoic acid, m. 182° (decomposition). Reduction of IV with Zn in AcOH gives a quant. yield of 3,4,2,6-Ac(MeO)(HO)2C6HAc, m. 105°. I (2.2 g.), 1.5 g. Zn(CN)2, and 10 mL. HCN in 120 mL. ether, saturated with HCl, give 2 g. of the 3-formyl derivative (V); 2 g. V in 40 mL. MeOH, added (5 min.) to 20 mL. concentrated HCl and 10 mL. H2O containing 15 g. amalgamated Zn and heated 5 min., give 1.6 g. Me 2,4-dihydroxy-6-methoxy-3-methylbenzoate (VI), m. 202°, gives a violet FeCl3 reaction; hydrolysis of VI with aqueous KOH gives 2,5,1,3-Me(MeO)C6H2(OH)2, m. 124°. VI (0.75 g.) with HCN and Zn(CN)2 give 0.6 g. of the 5-formyl derivative, m. 122°, gives a brown-violet FeCl3 reaction; 2,4-dinitrophenylhydrazone, orange, m. 262-3° (decomposition). 3,5-(MeO)2C6H3OH (5 g.), 5 g. ZnCl2, 10 g. Cl3CCN, and 100 mL. ether, saturated at 5° with HCl and the products hydrolyzed after 24 h., give 3.7 g. α,α,α-trichloro-4-hydroxy-2,6-di-methoxyacetophenone (VII), pale yellow, m. 117°; with warm 2 N NaOH, VII gives a quant. yield of 4,2,6-HO(MeO)2C6H2CO2H, m. 201°; reduction of VII with Zn and HCl in MeOH gives a quant. yield of 2-ethylphloroglucinol 1,3-di-Me ether (VIII), m. 153°; 0.6 g. VII, 2 g. Zn, and 5 mL. AcOH, refluxed 30 min., give VIII; addition of 2 g. Zn (3 min.) to 0.6 g. VII in 5 mL. AcOH and heating 2 min. on the steam bath give a quant. yield of 4,2,6-HO(MeO)2C6H2Ac. 3,5-(MeO)2C6H2OH (2.5 g.) and 2 g. ZnCl2 in 50 mL. ether, saturated at room temperature with HCl, treated with 6 g. F3CCN, the product (after 4 h.) hydrolyzed (15 min.) with H2O, and the solid (1.5 g.) distilled with steam, give 0.2 g. α,α,α-trifluoro-2-hydroxy-4,6-dimethoxyacetophenone, bright yellow, m. 87° (red-brown FeCl3 reaction), and 1 g. α,α,α-trifluoro-4-hydroxy-2,6-dimethoxyacetophenone, m. 155°. 2,1,3,5-Me(MeO)C6H2(OH)2 (1.4 g.) gives 0.5 g. α,α,α-trifluoro-2,6-dihydroxy-4-methoxy-3-methylacetophenone, bright yellow, m. 145°, gives an intense violet-brown FeCl3 reaction. 2,3,1,5-Me(HO)C6H2(OMe)2 (1.1 g.) gives 0.75 g. α,α,α-trifluoro-2-hydroxy-4,6-dimethoxy-3-methylacetophenone, bright yellow, m. 100°, gives an intense green-brown FeCl3 reaction. 2-Methyl-3-trichloroacetylindole (0.5 g.) in 17 mL. MeOH containing 1 drop 60% KOH, refluxed 5 min., gives a quant. yield of Me 2-methyl-3-indolecarboxylate, m. 165°. 2,6-(HO)2C6H3Ac (2.5 g.) and 2 g. BrCH2CO2Et in 100 mL. Me2CO containing 20 g. K2CO3, refluxed 3 h., give 2.9 g. Et (2-acetyl-3-hydroxyphenoxy)acetate (IX), m. 74-5°, gives a deep crimson FeCl3 reaction; 1 g. ester, hydrolyzed (30 min.) on the steam bath with 10 mL. 2 N NaOH, the acid refluxed 80 min. with 2.5 g. AcONa and 8 g. Ac2O, and the ester hydrolyzed (1 h. on the steam bath) with 2 N NaOH, gives 0.4 g. 4-hydroxy-3-methylbenzofuran (X), m. 111°. X (2.1 g.), 4 g. ZnCl2, and 4 g. Cl3CCN in ether, saturated at 5° with HCl and the ketimine hydrolyzed with H2O, give 1.7 g. of the 2-trichloroacetyl derivative (XI), bright green, m. 159°; with EtOH containing a little 60% KOH XI yields 2-carbethoxy-4-hydroxy-3-methylbenzofuran (XII), m. 155°; 2 g. IX in 15 mL. EtOH containing EtONa (0.2 g. Na), refluxed 1 h., gives 0.2 g. XII. 2,4-(MeO)2C6H3COCF3 yields a 2,4-dinitrophenylhydrazone, orange, m. 195°; the dinitrophenylhydrazone of 6-methoxy-2-(trifluoroacetyl)benzofuran, blood-red, m. 190-1° (decomposition). The theor. implications of the bright color and the reactions of the α,α,α-trichloro-and α,α,α-trifluoropolyhydroxyacetophenones and their derivatives are discussed. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).HPLC of Formula: 65417-22-3
Methyl 2-methyl-1H-indole-3-carboxylate(cas:65417-22-3) belongs to indole. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. HPLC of Formula: 65417-22-3
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles