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ChemicalBook CAS DataBase List 3-Methyl-4-nitropyridine N-Oxide
1074-98-2

3-Methyl-4-nitropyridine N-Oxide synthesis

4synthesis methods
Nitration of picoline-N-oxide in the fourth position yields 3-Methyl-4-nitropyridine N-Oxide. Initially, Picoline-N-oxide (50 g) was melted at 38C and mixed with sulfuric acid (250 ml) in cold condition. Later, nitration of this mixture was done at room temperature by addition of sodium nitrate (70 g) and the solution was continuously stirred until all the solid particles dissolves. Temperature was increased slowly to 70C by keeping it in an oil bath and solution was stirred continuously for 2 h at this temperature. To ensure complete nitration, the solution was maintained about 95–100C for 12 h with continuous stirring. The reaction mixture was taken out from the oil bath and cooled. It is then poured over crushed ice and neutralized with ammonia solution till the pH reaches about 7–8. On cooling, bright yellow crystalline 3-Methyl-4-nitropyridine N-Oxide powder was obtained. It was washed and dried in vacuum[1].
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Yield:-

Steps:

Multi-step reaction with 2 steps
1: dihydrogen peroxide / acetic acid / 70 °C / Cooling with ice
2: nitric acid / sulfuric acid / 2 h / 0 - 100 °C

References:

DAIICHI SANKYO COMPANY, LIMITED;VERMA, Ashwani, Kumar;NAGASWAMY, Kumaragurubaran;SHARMA, Lalima;GHOSH, Soma;KALE, Balkrishna, Ramchandra;MONDAL, Aniruddha;SRIVASTAVA, Punit, Kumar;DASTIDAR, Sunanda, Ghosh;MIYAUCHI, Rie;MURATA, Takeshi;ISHIZAKI, Masayuki;NAGAMOCHI, Masatoshi;IIMURA, Shin;MOMIN, Rijwan, Jaffer;WAGH, Pradip, Balu;PANSARE, Sonali, Nanasaheb;MARKAD, Pramod, Raosaheb;KHAIRNAR, Yogesh, Balasaheb WO2012/160464, 2012, A1

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