2,3-Dimethyl-3H-imidazo[4,5-c]pyridine (cas: 52538-09-7) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Name: 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine
Imidazoles. IX. A new preparation of N-alkylated imidazole compounds was written by Weidenhagen, Rudulf;Train, Gert;Wegner, Hans;Nordstrom, Ludwig. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1942.Name: 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine The following contents are mentioned in the article:
A solution of 2 g. Cu(OAc)2, 2 cc. 40% HCHO and 30 cc. H2O at 0° is treated with 1 g. ο-H2NC6H4NHMe.2HCl in 15 cc. 50% alc. at 0°; the CuCl salt precipitates immediately and the reaction is completed by heating 10 min. at 75°; decomposition with H2S in dilute HCl gives the HCl salt, which is liberated by K2CO3; the yield of 1-methylbenzimidazole (I) is 67%; AcH gives 83% of the 2-Me derivative of I; EtCHO yields the 2-Et derivative, very hygroscopic, m. 61.5-2.5° (containing 0.79 mol. H2O), m. 54.5-5.5° (anhydrous); picrate, m. 235-6°; iso-PrCHO gives 84% of the 2-iso-Pr derivative, b0.3 116-18° (picrate, yellow, m. 225-6°); BzH gives 87.5% of the 2-Ph derivative; p-MeOC6H4CHO yields 77.5% of the 2-(p-methoxyphenyl) derivative, m. 118°; 2-(p-nitrophenyl) derivative, yellow, m. 213-14°, 88%; 2-(2-furyl) derivative, with 0.5 mol. H2O, m. 78° (anhydrous, m. 56°), 85%. ο-O2NC6H4NHEt with SnCl2 in HCl gives 69% of N-ethyl-ο-phenylenediamine (II), m. 185-7° (decomposition). II, HCHO and Cu(OAc)2 give 71% of 1-ethylbenzimidazole (III); AcH yields 90% of the 2-Me derivative of III, b0.3 110-12° (picrate, m. 236-7°); EtCHO gives 74% of the 2-Et derivative of III, b0.2 106.5-7.5° (HCl salt, m. 168.5-9.5°; picrate, m. 207°); BzH yields 82% of the 2-Ph derivative of III; 2-(p-methoxyphenyl) derivative, m. 106-6.5°, 90%; 2-(m-nitrophenyl) derivative, m. 117.5-18°, 46%. ο-ClC6H4NO2 and PrNH2 in EtOH, heated 7 hrs., give 97% of N-propyl-ο-nitroaniline, red oil; reduction yields 57% of N-propyl-ο-phenylenediamine-2-HCl (IV), m. 172-3° (decomposition). IV, HCHO and Cu(OAc)2 give 62% of 1-propylbenzimidazole (V), analyzed as the picrate, m. 180-1°; IV and AcH give 92% of the 2-Me derivative of V, hygroscopic oil, b0.2 111-12° (picrate, m. 218-19°); 2-Et derivative, 85%; picrate, m. 212-12.5°; 2-(p-methoxyphenyl) derivative, m. 67.5-8°. 3-Amino-4-(methylamino)pyridine (VI), m. 169°, results in 95% yield on reduction of the 3-NO2 compound with Fe in AcOH (picrate, m. 184°; HCl salt, m. 221°). VI (1.8 g.), 1 cc. AcH and 6 g. Cu(OAc)2 in 50 cc. 50% EtOH, heated 3 hrs. at 150°, give 50% of 1′,2′-dimethylimidazolo-4′,5′,3,4-pyridine (VII), m. 174° (picrate, m. 204-5°); EtCHO gives 48% of the 2′-Et analog of VII, with 1.5 mols. H2O, m. 76°; 2′-Pr analog, with 1.5 mols. H2O, m. 64°, 59%; 2′-hexyl analog, a hygroscopic oil, analyzed as the dioxalate, m. 140°, 47%; 2′-Ph analog, m. 149°, 49% (hydrated, m. 79-80°); 2′-(2-furyl) analog, m. 173°, 57%. 3-Amino-4-(ethylamino)pyridine, AcH and Cu(OAc)2 in EtOH, heated 4.5 hrs. at 150°, give 1′-ethyl-2′-methylimidazolo-4′,5′,3,4-pyridine, m. 84°; with 1 mol. of H2O, m. 40°; picrate, m. 191°; 2′-Et analog, hygroscopic oil; with 2 mols. H2O, m. 52°, 54%; 2′-Pr analog, very hygroscopic oil, 39%; with 2 mols. H2O, m. 68°; 2′-(p-methoxyphenyl) analog, m. 142°, 71%; 2′-(2-furyl) analog, pale yellow, m. 125°, 68%. 3-Nitro-4-(propylamino)pyridine, in nearly theoretical yield by boiling 3-nitro-4-methoxypyridine with PrNH2 in EtOH; 3-NH2 derivative, with 1 mol. H2O, m. 93°, 78%. 1′-Propyl-2′-methylimidazolo-4′,5′,3,4-pyridine, analyzed as the picrate, yellow, m. 156.5-7.5°; 1′-Bu analog, with 2 mols H2O, m. 47°, 58%. This study involved multiple reactions and reactants, such as 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine (cas: 52538-09-7Name: 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine).
2,3-Dimethyl-3H-imidazo[4,5-c]pyridine (cas: 52538-09-7) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Name: 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem