The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The directive influence of the N-oxide group during the nitration of derivatives of pyridine N-oxide. IV. Nitration of 3-bromo-5-methoxy- and 3,5-dimethoxypyridine N-oxide》. Authors are den Hertog, H. J.; van Ammers, M.; Schukking, S..The article about the compound:5-Bromo-3-methoxypyridin-2-aminecas:42409-58-5,SMILESS:BrC1=CN=C(C(=C1)OC)N).Application of 42409-58-5. Through the article, more information about this compound (cas:42409-58-5) is conveyed.
3,5-Dibromopyridine heated with NaOMe in the presence of Cu powder in a sealed tube for 48 hrs. at 110°, yielded 3-methoxypyridine, 3,5-dimethoxypyridine (I), b0.2 66-8° [picrate, m. 146.5-7.0°; N-oxide (II), m. 91-3°; II picrate, m. 131-2°], and 3-bromo-5-methoxypyridine (III), m. 32-3° [picrate, m. 159-60°; N-oxide (IV), m. 200-1°]. To a solution of IV in H2SO4, KNO3 was added in small portions at room temperature; the mixture kept at 30-5° 24 hrs. gave 3,5,6-Br(MeO)(O2N)PNO (V), m. 164.5-6.0°. Similar nitration of II at 0° gave 2,3,5-O2N(MeO)2PNO (VI), m. 169-71°. Similarly 3-bromo-5-methoxy-6-nitropyridine (VII), m. 111.5-12.0°, is obtained from III. Reduction of V with Fe and HOAc gave 6-amino-3-bromo-5-methoxypyridine, m. 84.5-5.0° [Ac derivative, 113.5-14.5°; picrate, m. 235-6° (decomposition)], also obtained by reduction of VII. Similar reduction of VI gave 2-amino-3,5-dimethoxypyridine (VIII), m. 69-70° (picrate, m. 236-6.5°). Nitration of III with a 1:1 mixture of H2SO4 and fuming HNO3 at 75° gave 3-bromo-5-methoxy-2,6-dinitropyridine, m. 103.5-4.5°. Nitration of I with H2SO4 and concentrated HNO3 at 70° gave 3,5-dimethoxy-2-nitropyridine which on reduction gave VIII. Bromination of 2-amino-3-ethoxypyridine gave 6-amino-3-bromo-5-ethoxypyridine, m. 96.5-7.0°. The ultraviolet absorption spectra of the compounds are reported.
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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem