Related Products of 13194-68-8, 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. 13194-68-8, name is 4-Iodo-2-methylaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
4-iodo-2-methylbenzenamine 24 (233mg, 1 mmol ) on reaction with l-rert-butyl-4-ethynylbenzene (25b, 158 mg,l .mmol) by employing Sonagashira coupling conditions using Pd(PPh3)4 (69.3 mg, 0.06 equiv) as catalyst, Cul (22.8 mg, 0.12equiv) as cocatalyst, butyl amine (261 mg, 3 equiv)as base and ether as solvent and kept the reaction for 6h. After completion of the reaction as indicated by TLC and the reaction mixture is extracted into ether (4×25 mL) from the aqueous layer and concentrated in vacuo. The compound was further purified by column chromatography using 60-120 silica gel (ethyl acetate/hexane,l:9) to obtain 4-((4-tert-butylphenyl) ethynyl)-2-methyl benzene amine (26b) as pure product. Anthranilic acid (27, 137 mg, lmmol) on reaction with acetic anhydride at 150 C and reflux for 30 min, after completion of reaction aqueous sodium bicarbonate solution is added and extracted in ethyl acetate (4×25 mL) from the aqueous layer and concentrated in vacuo afforded 2-methyl 4H- benzo [cf] [l,3]oxazin-4-one compound (28) as pure product. To a stirred solution of 4-((4-tert- butylphenyl)ethynyl)-2-methylbenzenamine (26b, 263 mg, 1 mmol) with 2-methyl-4H- benzo[c ][l,3]oxazin-4-one (28, 161 mg, lmmol) in acetic acid and reflux for 8h After com pletion of the reaction as indicated by TLC. then the reaction mixture was quenched with NaHC03 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2S04 afforded 3-(4-((4-iert-butylphenyl)ethynyl)-2-methylphenyl)-2-methylquinazolin-4(3H)-one (29b). Reaction of 3-(4-((4-terf-butylphenyl)ethynyl)-2-methylphenyl)-2-methyl quinazolin-4(3H)-one (29b, 406 mg, lmmol) with 2,4-dihydroxybenzaldehyde (30d, 138 mg, lmmol) was taken in acetic acid Then the resulting mixture was stirred under reflux conditions for 8 h and then the reaction mixture was quenched with NaHC03 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2S04.The resulting product (5d) was purified by column chromatography employing EtOAc/Hexane as an eluent.Mp 93-95 C; JH NM R (CDCI3+DMSO-d6, 200 MHz) delta 8.23 (d, J = 15.9 Hz, 1H), 8.20 (s, 1H), 7.79-7.66 (m, 3H), 7.51-7.34 (m, 6H), 7.26 (s, 1H), 7.10 ( d, J = 8.3 Hz, 1H), 6.89 (d, J = 8.3 Hz, 1H), 6.21 (d, J = 15.2 Hz, 1H), 6.18 (s, 1H), 2.06 (s, 3H), 1.14 (s, 9H); LRMS(ESI, m/z) 527 (M)+
The synthetic route of 4-Iodo-2-methylaniline has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CONCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; KAMAL, Ahmed; SULTANA, Farheen; BHARATHI, Erla Vijaya; SRIKANTH, Yellamelli Valli Venkata; VISWANATH, Arutla; SWAPNA, Ponnampalli; WO2012/111017; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com