What is the best reagent which can be useful in the reduction of 2,4-dinitrobenzaldeyde?
Check this useful paper instead of your phone
Org. Proc. Res. Dev., 2001, 5 (5), pp 539–541
Already answered this question. Seems have been banned in my answer.
Check this ref: Org. Proc. Res. Dev., 2001, 5 (5), pp 539–541 (instead of your cellphone)
After succeeding your quest, if you plan to scale-up such reaction, you must be aware that some conditions (catalysts , solvants..) could generate hazardous intermediate (type n-oxyde, diazo..). Some usefull articles can be found in OPRD. Good luck.
You could use iron turnings and sulfuric acid, good luck and I will send some research papers concerning this matter.
Thanks for the answering and it will be interesting to know that finally my reaction is no w completed (Fe+H2SO4). But I am getting two spots on the TLC and Both are products.
You could have get the aldehyd and some imine formed between two molecule of the aldehyd.
According to my experience the best way to reduce nitrobenzene to aniline is reduction by activated zinc dust+acetic acid in DCM.
Activation of Zn dust: 400 g Zn dust is taken in a flask 150 mL of 10% HCl aq. soln. was added stirred for 2 minute, filtered washed with 300 mL water followed by 100 mL acetone, dried in vacuum oven.
Procedure for reduction: To a stirred soln of nitrobenzene derivatives (A) (1 equiv) in DCM 5 mL/mmol of A) activated Zn-dust (50 equiv.) was added, cooled to 0 degree centigrade. AcOH (1.5 mL/ mmol of A) was added dropwise. Stirred for 10 min. (completion of the rxn to be checked by TLC analysis) at 0 degree, filtered through a pad of celite (DCM evaporated) and the celite was washed with EtOAc. The filtrate was neutralized with NaHCO3 soln. dried and purified by column. Try this method I think it will serve your purpose.
It's better to protect the Aldehyde with MeOH or EtOH in a mild acidic media, and then reduce the Nitro groups with Tin and HCL (Conc).
You can use Fe in HCl for reduction of 2,4-dinitrobenzaldehyde chiefly or H2/Pt can be used.
SnCl2/EtOH/heat - simple and efficient. You will need to filter through celite super cell during the extraction stage as emulsions form.
Tet Lett. 1984, Vol. 25., No.8, pp 839-842
Catalytic reduction of nitro group to amine by hydrogenation in the presence of Pd or Pt catalyst using EtOH+ small quantitty of AcOH as a solvent. It will be superior over using SnCl2/EtOH in work-up.
you can you use mild reducing agent such as : Zn dust in HCl and reflux. I'm afraid if you used Pt or Pd you might reduce aldehyde to alcohol.
The best way to do it: Nitro compound in a mixture of EtOH and H2O; iron powder and CaCl2. The resulting suspension was stirred at 60 °C.
please check this paper: Synlett 2010, No. 20, 3019–3022.
Can Mohan Tirumalasetty give a reference for the method he proposes please.
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