4-Methyl-3-nitropyridine

Chemical Properties

Deliquescent cryst

Uses

4-Methyl-3-nitropyridine may be used as a starting material in the synthesis of ethyl 6-azaindole-2-carboxylate and also 3-substituted azaindoles.

Uses

4-METHYL-3-NITROPYRIDINE is a useful research chemical.

General Description

4-Methyl-3-nitropyridine, a substituted nitropyridine, can be prepared by the malonation of 4-methoxy-3-nitropyridine with sodium diethyl malonate.

Synthesis

The general procedure for synthesizing 3-nitro-4-methylpyridine from 4-methylpyridine is as follows:1) In step 1) of Example 1, prepare a reaction solution by adding 60 g of nitrogen pentoxide solid to 300 g of liquid sulfur dioxide at -30° C. and stirring sufficiently until completely dissolved.2) Dissolve 30 g of 4-methylpyridine in 120 g of liquid sulfur dioxide and maintain the temperature at -30° C.3 ) Slowly drop the reaction solution into 300 g of ice water for 5 minutes. ) Slowly add the nitrogen pentoxide-sulfur dioxide solution prepared in step 1) dropwise to the 4-methylpyridine solution, and react for 5 min. 4) Slowly pour the reaction solution into 300 g of ice water, and hydrolyze thoroughly. 5) Adjust the pH of the hydrolyzed solution to 8-9 using sodium carbonate. 6) Add 290 g of toluene for two extractions, and combine the extracts. 7) Remove the solvent by vacuum distillation to obtain 39 g of 3- Nitro-4-methylpyridine. The purity of the product was 99.0% by gas chromatography.

References

[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 538 - 541
[2] Acta Chemica Scandinavica, 1994, vol. 48, # 12, p. 1001 - 1006
[3] Acta Chemica Scandinavica, 1994, vol. 48, # 2, p. 181 - 182
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 6, p. 1211 - 1216
[5] Acta Chemica Scandinavica, 1996, vol. 50, # 6, p. 556 - 557