Leída el 29 de mayo de 2009. I tried to search literature, but workup process was different depending on materials. Yahoo ist Teil von Verizon Media. Please try iron hydrochloride method if your entity consist of multi-substituents, in that case Sn or SnCl2 is insufficient, and usually yields multi products. You could write this in a more condensed form as: \[ C_6H_6 + HNO_3 \rightarrow C_6H_5NO_2 + H_2O\]. aus oder wählen Sie 'Einstellungen verwalten', um weitere Informationen zu erhalten und eine Auswahl zu treffen. The reaction should proceed with a some heating, up to about 30-40 0C, Moscow Institute of Physics and Technology. See Nomenclature of Organic Compounds for a review on naming and priority rules. Missed the LibreFest? All rights reserved. It makes it possible to obtain nitroaromatic compounds, which may be of interest, but they are essentially intermediate compounds. To reduce NO2 to NH2 without affect any other group by the use of catalytic hydrogenation using PtO2 /H2 in acetic acid. I would like to convert the nitro group to amino group. The electrons come from the tin, which forms both tin(II) and tin(IV) ions. I used Sn/HCl with nitro compound and SnCl2/HCl in EtOH for the reduction from NO2 to amine. One of my aldehyde, the other should be alcohol (much more polar) and the last one I'm not sure what it is. It was one of the first chemical processes used to functionalize an aromatic derivative. How do I improve the yield of a carboxylic acid/amine coupling with EDC/DMAP at RT in DCM? BH4- is a … SnCl2 or Sn? There a long discussion of the pro's and con's of different nitro reduction reagents on Researchgate in the link. Be aware that the work-up may be challenging. Total Synthesis of (−)-C 10 -Desmethyl Arteannuin B, Totalsynthese optisch aktiver Steroide, X. Reduktion von 3Methoxy8,14-seco-1,3,5(10),9-östratetraen-14, 17-dion mit chiralen komplexen Hydriden. Could this be the work up procedure (co-precipitation) or scale of crystallization...any ideas? Which one is the best procedure for the reduction of aromatic nitro compounds? Another option would be using Raney-Ni (becareful when use Ra-Ni!!). Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a temperature not exceeding 50 C. As temperature increases there is a greater chance of getting more than one nitro group, -NO 2 , substituted onto the ring. The simplest case. May I know the most suitable molar ratio of the SnCl2 with the -nitro group/HCl? May I know the most suitable molar ratio of the SnCl2 with the -nitro group/HCl? Good luck. Because i used Fe with NH4Cl in ethanol with controlled heat condition. the simplest and greener method is the Hydrogenation (1 atm of H2) using Pd/C at 0-10°C. SN , RANEY NICKEL OR .YOU CAN ALSO USE HYDRAZINE AT 0-10 TEMP. You would reflux the benzene with sulferic acid and nitric acid. I used this methodology Fe powder (5eq), Ethanol: Water/4:1, Con HCl (1V) @ 90°C. Synthesis and comparison of various dithiols as reducing agents for disulfides [microform]. Palladium catalyzed hydrogenation at atmospheric pressure is the best way I guess. NH2 -> NO2 Crazy idea So here is a crazy idea for a Trinitrotoluene (TNT) synthesis. Filter hot. In your case it seems that the product can be distilled in high vacuum. I. Does anyone have suggestions other than Raney Ni, Pd/C, Sn/HCl, Fe/HCl? The concentrated sulphuric acid is acting as a catalyst. There is one paper using SnCl2 instead of Sn in the same condition. This page looks in outline at the preparation of phenylamine (also known as aniline or aminobenzene) starting from benzene. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. And how about when I have multiple substituents on my benzene? Anna University of Technology, Tiruchirappalli. Also it looks like your compound is set up for cyclization to a 4-quinolinone. I have thought of carrying out the reaction at lower temperatures. How to reduce NO2 to NH2 without affect any other group in following reaction? To menu of electrophilic substitution reactions. Finally I add one more eq. What is the procedure of the reduction from NO2 to NH2 using Sn or SnCl2? Does anyone have suggestions other than Raney Ni, Pd/C, Sn/HCl, Fe/HCl? For more information contact us at email@example.com or check out our status page at https://status.libretexts.org. Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a temperature not exceeding 50°C. Benzene is treated with a mixture of concentrated nitric acid and concentrated sulphuric acid at a temperature not exceeding 50°C. © 2008-2020 ResearchGate GmbH. 9307571. I have difficulty in workup process. Under the acidic conditions, rather than getting phenylamine directly, you instead get phenylammonium ions formed. Legal.