| Identification | Back Directory | [Name]
6-Aminonicotinaldehyde | [CAS]
69879-22-7 | [Synonyms]
6-Aminonicotildehyde
6-Aminonicotinaldehyde
2-aMino-5-forMylpyridine
6-Amino-pyridine-3-carbaldehyde
6-aMino-3-Pyridinecarboxaldehyde
6-Aminopyridine-3-carboxaldehyde
3-Pyridinecarboxaldehyde, 6-amino-
6-aMinonicotinaldehyde hydrochloride
6-aMinonicotinaldehyde
6-aMinonicotinaldehyde hydrochloride | [Molecular Formula]
C6H6N2O | [MDL Number]
MFCD09757481 | [MOL File]
69879-22-7.mol | [Molecular Weight]
122.12 |
| Chemical Properties | Back Directory | [Melting point ]
161℃ | [Boiling point ]
309.0±27.0 °C(Predicted) | [density ]
1.264±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [pka]
4.78±0.13(Predicted) | [Appearance]
Light yellow to yellow Solid |
| Hazard Information | Back Directory | [Uses]
6-Aminopyridine-3-carboxaldehyde is a novel ribonucleotide reductase inhibitor that belongs to the class of metal-binding site affecting ribonucleotide inhibitors that are derivatives of alpa-hetero
cyclic carboxaldehyde thiosemicarbazone. | [Synthesis]
General procedure for the synthesis of 2-amino-5-formylpyridine from 2-amino-5-cyanopyridine: To a solution of 2-amino-5-cyanopyridine (10 g, 83.95 mmol, 1 eq.) in tetrahydrofuran (THF, 150 mL) was slowly added lithium aluminum hydride (LAH, 6.37 g, 167.90 mmol, 2 eq.) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 1.5 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated sodium sulfate solution at 0 °C followed by the addition of water (100 mL). The reaction mixture was extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed with saturated brine (30 mL × 1), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-amino-5-formylpyridine (7.50 g, 61.42 mmol, 73.16% yield) as a yellow oil.LCMS (ESI) analysis: m/z [M + H]+ Theoretical value for C6H6N2O was 123; measured value 123; retention time (RT) = 0.099 min. | [References]
[1] Patent: WO2018/209132, 2018, A1. Location in patent: Paragraph 0458; 0489
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 292 - 300
[3] Patent: US2009/143420, 2009, A1. Location in patent: Page/Page column 7
[4] Patent: EP1724263, 2006, A1. Location in patent: Page/Page column 55
[5] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0177; 0178 |
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