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| | 4-Nitro-pyridin-2-ylamine Basic information |
| | 4-Nitro-pyridin-2-ylamine Chemical Properties |
| Melting point | 96 °C | | Boiling point | 339.0±22.0 °C(Predicted) | | density | 1.437±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | form | solid | | pka | 3.43±0.11(Predicted) | | color | Light yellow to orange | | CAS DataBase Reference | 4487-50-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Safety Statements | 22-24/25 | | HS Code | 2933399990 |
| | 4-Nitro-pyridin-2-ylamine Usage And Synthesis |
| Uses | 4-Nitropyridin-2-amine is used to synthesize tetrahydronaphthalene Raf inhibitors. | | Synthesis | Step 3: Synthesis of 4-nitropyridine-2-amino intermediate-22
N-(4-methoxybenzyl)-4-nitropyridin-2-amine (Int-21, 27.8 g, 0.11 mol) and anisole (13 mL, 0.12 mol) were dissolved in trifluoroacetic acid (112 mL) and the reaction was heated at 80 °C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated. The resulting residue was ground with EtOAc and hexane to give a pale yellow solid, which was separated by filtration. The filtrate was allowed to stand overnight to precipitate a second batch of crystals. The two solid batches were combined, dissolved in 1N NaOH solution (250 mL) and extracted with EtOAc (2 x 250 mL). The organic phases were combined, dried over magnesium sulfate, filtered and concentrated to give 4-nitropyridin-2-amine as an orange solid (10.2 g, 67% yield).
LCMS (FA) ES+: m/z 140.
1H NMR (400 MHz, CD3OD) δ ppm: 8.15 (dd, J = 5.7, 0.6 Hz, 1H), 7.23 (dd, J = 2.0, 0.6 Hz, 1H), 7.20 (dd, J = 5.7, 2.0 Hz, 1H). | | References | [1] Patent: WO2011/146591, 2011, A1. Location in patent: Page/Page column 72-73
[2] Patent: US2012/15942, 2012, A1. Location in patent: Page/Page column 51
[3] Patent: EP3305788, 2018, A1. Location in patent: Paragraph 0059; 0062
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 6, p. 1836 - 1846 |
| | 4-Nitro-pyridin-2-ylamine Preparation Products And Raw materials |
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