3-Nitro-2-pyridinecarboxaldehyde

3-Nitro-2-pyridinecarboxaldehyde - Names and Identifiers

Name	3-Nitropyridine-2-Carbaldehyde
Synonyms	3-nitropicolinaldehyde 3-nitropyridin-2-carbaldehyde 3-Nitropyridine-2-Carbaldehyde 3-Nitro-2-Pyridincarboxaldehyd 3-Nitropyridine-2-carboxaldehyde 3-Nitro-2-pyridinecarboxaldehyde 2-Pyridinecarboxaldehyde, 3-nitro-
CAS	10261-94-6

3-Nitro-2-pyridinecarboxaldehyde - Physico-chemical Properties

Molecular Formula	C6H4N2O3
Molar Mass	152.11
Density	1.432±0.06 g/cm3(Predicted)
Boling Point	283.2±25.0 °C(Predicted)
pKa	-1.20±0.10(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

3-Nitro-2-pyridinecarboxaldehyde - Reference Information

Application

3-nitropyridine-2-formaldehyde can be used as an intermediate in pharmaceutical synthesis, which can be used by 2-Chloro-3-nitropyridine is used as the reaction raw material to react with tributylvinyltin to prepare the intermediate 3-nitro-2-vinylpyridine, it is further prepared under the action of 4-methylmorpholine-N-oxide.

preparation

step 1: 3-nitro -2-vinylpyridine dissolves 2-chloro -3-nitro-pyridine (20g,126.15mmol) into 1,4 dioxane (378mL), adding tributylvinyltin (48g,151.38mmol), degassing the reaction mixture with nitrogen for 30 minutes, adding bis (triphenylphosphine) palladium (II) chloride (4.4g,6.3mmol) to the reaction mixture, stirring overnight at 110°C. The reaction mixture was cooled to room temperature, water was added and extracted with EtOAc. The organic layer was washed with brine and dried with Na2SO4, the organic layer was concentrated in vacuum and purified by silica gel column chromatography, eluted with 0-5%EtOAc hexane solution to give 3-nitro-2-vinylpyridine. Step 2: 3-Nitropyridine-2-Formaldehyde Dissolve 3-Nitro-2-vinylpyridine (14g,93.25mmol) in THF:H2O(2:1)(560mL) and add 4-Methylmorpholine-N-oxide (16.3g,139.87mmol), tert-butanol (1mL) and osmium tetroxide (4%,2mL). The reaction mixture was stirred at 25°C for 5h to form diol, sodium metaperiodate (64.87g,279.7mmol) was added to the reaction mixture, and stirred at 25°C for 8h. The reaction mixture was filtered by diatomite and washed with EtOAc, the filtrate was extracted with EtOAc, the organic layer was washed with brine and dried with Na2SO4, and concentrated to obtain 3-nitropyridine-2-formaldehyde.

Last Update：2024-04-09 21:01:54