Synthetic Route of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Phosphorus oxychloride (1.47 g, 9.6 mmol, 0.9 mL) was added dropwise at -10 C to a stirred pyridine (40 mL) solution of N-Boc-L-proline 7 (1.74 g, 8.08 mmol) and arylamine 6 (2.24 g, 8.08 mmol) under argon atmosphere. The reaction mixture was stirred for 30 min (-10-5 C), then poured into water (200 mL) containing ice, and extracted with EtOAc. The aqueous layer was additionally extracted with EtOAc. The extract was washed with water, saturated NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using CHCl3 as the eluent. The isolated product with Rf 0.56 (EtOAc/LP, 1 : 2) was crystallized from petroleum ether to give amide 8 (2.8 g, 74%) as light brown crystals, m.p. 92-95 C, [alpha]23D -103.96 (c = 1.0, CHCl3). 1H NMR (CDCl3), delta: 1.35 and 1.49 (both br.s, integral ratio of 5/4, 9 H, Me3C); 1.74-2.42 (m, 4 H, HC(4), HC(5)); 3.39-3.80 (m, 2 H, HC(3)); 3.91 (s, 3 H, MeO); 4.27 and 4.41 (both m, integral ratio of 5/4, 1 H, HC(1)); 7.81 (br.d, 1 H, HC(3), J = 8.2 Hz); 8.34 (br.s, 1 H, HC(4)); 8.57 (br.d, 1 H, HC(6), J = 8.2 Hz); 11.43 (m, 1 H, HN) (mixture of rotamers, see Ref. 21).
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 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com