Nitration of 6-hydroxynicotinic acid and related compounds was written by Berrie, A. H.;Newbold, G. T.;Spring, F. S.. And the article was included in Journal of the Chemical Society in 1951.Related Products of 59237-53-5 This article mentions the following:
The following study is a part of a projected synthesis of lysergic acid. 6-Hydroxynicotinic acid (I) (50 g.) in 500 cc. HNO3 (d. 1.52), kept 4 hrs. at 45-50°, gives 20 g. 5-nitro derivative (II), yellow, m. 278° (decomposition), absorption maximum at 2110 and 3600 A. (ε 19,200 and 7900); Me ester, pale yellow, m. 206°, 65%; Et ester, pale yellow, m. 165-7°. I (2 g.) in 20 cc. HNO3 (d. 1.52), refluxed 30 hrs., gives 1 g. 3,5-dinitro-2(1H)-pyridone (III), yellow, m. 175°, absorption maximum at 2140 and 3260 A. (ε 13,400 and 11,400); 1 g. II and 10 cc. HNO3, heated 30 hrs., give 0.5 g. III; 0.92 g. 2-amino-3,5-dinitropyridine and HNO2 and later, NaOH, give 0.8 g. III; 1 g. 3-nitro-2(1H)-pyridone, refluxed 2 hrs. with HNO3, gives 0.3 g. III; 5-nitro-2(1H)-pyridone yields 38% III. 1,6-Dihydro-6-oxo-1-methylnicotinic acid (IV) (3.06 g.) and 30.6 cc. HNO3 (d. 1.52), heated 5 hrs. at 50-5°, evaporated to dryness, and crystallized from H2O, gave 2.0 g. 1-methyl-3,5-dinitro-2(1H)-pyridone (V), pale yellow, m. 178°, absorption maximum at 2080, 2180, and 3100 A. (ε 20,600, 19,100, and 12,700); acidification of the filtrate (concentrated HCl) gives 15.8% of the 5-NO2 derivative (VI) of IV, yellow, m. 217-22°, absorption maximum at 2180 and 3640 A. (ε 18,100 and 6600); Me ester, yellow, m. 147-9°; Et ester, pale yellow, m. 124°. IV (3.06 g.) and 30.6 g. HNO3 (d. 1.52), refluxed 5 hrs., give 2 g. V; 0.25 g. VI and HNO3, refluxed 4 hrs., give 0.2 g. V. 1-Methyl-3-nitro-2(1H)-pyridone (0.7 g.) and HNO3, refluxed 2 hrs., give 0.3 g. V; 0.7 g. of the 5-NO2 isomer yields 0.3 g. V; 0.92 g. III and 0.28 g. KOH in 10 cc. H2O, evaporated to dryness and heated 3 hrs. at 120° with MeI in MeOH, give 0.5 g. V. II (1.84 g.), heated 20 hrs. at 100° with 10 cc. PBr3 and 6.4 g. Br and the bromide decomposed with 20 cc. MeOH, gives 1.6 g. Me 6-bromo-5-nitronicotinate (VII), pale yellow, m. 98°; Et ester, pale yellow, m. 85°. II (0.92 g.), heated 2 hrs. at 100° with PCl5, and POCl3, gives 0.92 g. of the 6-Cl analog of VII, pale yellow, m. 76°; Et ester, m. 61°, 44%. III(0.92 g.),1.5 g. PCl5, and 2 cc. POCl3, heated 2 hrs. at 120°, give 0.5 g. 2-chloro-3,5-dinitropyridine, m. 64.5°. 2-Amino-5-chloro-3-nitropyridine (1.25 g.) in 4 cc. H2SO4 (d. 1.84) and 2.5 cc. H2O, treated with I g. NaNO2 (below 10°), stirred 1 hr., diluted with 25 cc. H2O, and kept overnight at 0°, gives 1.18 g. 5-chloro-3-nitro-2(1H)-pyridone (VIII), yellow, m. 235°; 1.75 g. VIII in 10 cc. 6% aqueous KOH, evaporated to dryness and heated 2 hrs. with 4 g. MeI in 10 cc. EtOH, gives 0.5 g. of the 1-Me derivative of VIII, pale yellow, m. 126°. 2-Amino-5-nitropyridine (1.39 g.) in 100 cc. EtOH, treated (ice cooling) with 0.71 g. Cl, gives 0.85 g. 2-amino-3-chloro-5-nitropyridine (IX), pale yellow, m. 211-13°. IX (0.35 g.) through the diazo reaction in H2SO4 gives 0.2 g. 3-chloro-5-nitro-2(1H)pyridone (X), pale yellow, m. 198°. V (1 g.), 3 g. PCl5, and 2 cc. POCl3, heated 4 hrs. at 150°, give 0.5 g. unchanged V and 0.2 g. 3-chloro-1-methyl-5-nitro-2(1H)-pyridone (XI), pale yellow, m. 115°; 0.99 g. V and 5 cc. SOCl2, heated 5 hrs. at 140-50°, give 0.25 g. unchanged V and 0.4 g. XI; the K compound from 1.75 g. X, MeI, and EtOH, boiled 2 hrs., give 1.5 g. XI. 3-Nitro-2(1H)-pyridone (1.4 g.) in 10 cc. hot 5% NaOH gives 0.9 g. Na 3-nitro-2-pyridyl oxide (XII), with I mol. H2O, yellow, m. 340°, absorption maximum at 2580 and 3600 A. (ε 2400 and 6600). Na 5-nitro-2-pyridyl oxide, with 3 mols. H2O, yellow, m. 303° (decomposition), absorption maximum at 2060 and 3020 A. (ε 9100 and 10,500); Na 3,5-dinitro-2-pyridyl oxide (XIII), with 2 mols. H2O, m. 298° (decomposition), absorption maximum at 2100 and 3260 A. (ε 13,600 and 10,100); these 3 Na salts decompose violently when heated. Nitration of 2(1H)-pyridone by the method of Chichibabin and Shapiro (C.A. 18, 2394) gives a compound m. 286° (decomposition), believed to be a mixture of XII and XIII; further nitration gives a good yield of III. In the experiment, the researchers used many compounds, for example, Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5Related Products of 59237-53-5).
Methyl 6-chloro-5-nitronicotinate (cas: 59237-53-5) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Alkyl chlorides are versatile building blocks in organic chemistry. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available.Related Products of 59237-53-5
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics