Nitro to amine reduction by activated zinc

[@Jeshine033]

thankyou Sir, I am so glad finding your chanel on youtube. Very helpful

[@Dr.Mosharraf]

My pleasure

[@user-mp4bc9qp2x]

the word you're looking for is emulsion or supsension at 2:30

[@Dr.Mosharraf]

Thank you for your word help. Yes you are correct

[@flaplaya]

Arylcyclohexylamine Nice work very accurately made 👍

[@Dr.Mosharraf]

Thank you for your comment. I visited your channel and made your channel to my list. 🤪😜

[@waltersobchak7275]

Haven’t seen you in a long time

[@palaksingla8854]

Sir could you tell us how many equivalents of starting material one should take while performing reduction of nitro to amine.

[@Mp-jw1qg]

gallium, indium, tin amalgam suspended in a solution of ethanol and nitrostryrene with hcl in ethanol added dropwise to control exotherm affords the amine in high yield. hold 10 mins at 80c after addition and then cool. it works at very large scale for imine to amine as well.

[@Dr.Mosharraf]

Thank you. Good to know that. I never did though.

[@Mp-jw1qg]

@@Dr.Mosharraf me either, totally not to reduce my favorite nitrostyrenes lol

[@Dr.Mosharraf]

😜🤪😝

[@jimparsons6803]

Right. Iron. Well understood and useful rx.

[@Dr.Mosharraf]

Thank you for your comment and for your support.

[@patricksweetman3285]

Unless you have to work-up with Fe^3+ in basic solution.

[@libra777319]

Really nice video and explanation. To tell the truth I was searching for a methodology to do nitro reduction to amine. Do you think 8-hydroxy-5-nitroquinoline could be converted by this method to the corresponding amine? Thank you and again, great video!

[@Dr.Mosharraf]

Hello Francisco, thank you for your comment. I think you can give a shot to reduce nitro group to amine of your compound by using activated zinc in acetic acid. Maybe you can try in a small scale. If it doesn’t work then try with Iron powder in acetic acid. Still if it doesn’t work then use SnCl2 in Ethanol. But last method work up will be tricky. And you have to be patient to extract. You might see some white precipitation derived from Tin chloride. You may consider another thing. You can protect your hydroxyl group with methyl or any other protection group, then you may try reduction and then deprotect your hydroxyl group. Or you can start with 8-methoxy-5-nitroquinolone. Then reduce nitro to amine. Then deprotect the methoxy to hydroxy by using BBr3 in DCM at low temperature. I hope it will help you. Please subscribe and like and press bell 🔔 button to get more update about chemistry.

[@user-mp4bc9qp2x]

the first thing you should try is pd/c with hydrogen. very clean. reductions with metals are awful, stoichiometric metal is always a terrible work up.

[@Dr.Mosharraf]

@e…Thank you for mentioning H2, Pd/C method. I forgot to mention it. But keep in mind, if you have any halogen like bromo or iodo group then you shouldn’t try hydrogenation method.

[@crabcrab2024]

@@user-mp4bc9qp2x Yeah...and Fe is FAR from stochiometric. 😁 Palladium is our choice.

[@juanuskuiful]

Pd/C hydrazine reduction also is a good choice

[@dr.naveenawasthi9861]

Sir you are great. Kindly tell the calculation regrading for the synthesis of any chemical compound in lab

[@Dr.Mosharraf]

Okay I will do. Thanks for the comment

[@slavakuznetsov4966]

Not sure you need to go through the trouble of activating Zn for this reaction. For Gringard - yes, but here you add it to a strongly acidic environment already (AcOH or HCl) that will dissolve all the oxide coating.

[@Dr.Mosharraf]

I tried with inactivated zinc and got less yield. It may give internal intermediate which is not amine. I didn’t use Grignard reagent because my compound had carbonyl group. AcOH is weak acid probably not enough to activate insitu. Anyway if you think your reaction may not need activated zinc maybe you can try.

[@smmcknnn]

Great video! is the reaction air sensitive?

[@Dr.Mosharraf]

Any reduction reaction should be air sensitive. So this reaction should be done under argon or nitrogen.

[@almche8978]

Thank you doctor.could please tell me how can I prepare solution of brine from NaCl . (How many gram to water)? Thank you advance

[@Dr.Mosharraf]

Just add enough NaCl in water so that it doesn’t dissolve completely. That means make a saturated NaCl solution which will contain solid NaCl also.

[@almche8978]

@@Dr.Mosharraf ok thank you a lot

[@lrmackmcbride7498]

The classic method is devarda's alloy

[@Dr.Mosharraf]

Thank you for your comment. Honestly I didn’t know about it. The. I googled it and it does make sense.

[@palaksingla8854]

Sir can you share how much equivalent of reactants you had taken for reaction to proceed.

[@Dr.Mosharraf]

Didn’t I mention the equivalent? Okay I have to search my electronic notebook. Once I see I will update.

[@palaksingla8854]

​@@Dr.Mosharraf Ok sir

[@palaksingla8854]

One more question sir, do all the starting material is consumed in reaction, Actually today I have performed reduction of nitro group in lab by following your procedure but after 3 hours of reaction I saw product was formed but very little amount of starting material was still present while monitoring tlc. Should I further run reaction for more time or do work up?

[@ВалерийСтраннов]

cool video, but use another stiring magnet

[@Dr.Mosharraf]

Thanks …good idea

[@ikehu4674]

Can I replace the argon to N2 in this experiment? THX

[@Dr.Mosharraf]

Yes you can. But make sure that Nitrogen is pure and dry.

[@patricksweetman3285]

You promised to show us the work-up.

[@Dr.Mosharraf]

Hi Patrick I already have described about the work up. Just filter the liquid from zinc and wash out with Ethyl acetate. Then remove the solvent with rotovap. Then add ethyl acetate in the crude and add sodium bicarbonate aqueous solution and extract with EtOAc couple of times. Also take the solid zinc part in the filter paper in a beaker and add NaHCO3 solution carefully (it will be reacting). Extract it with EtOAc. Combined all organic layer and do the rotovap. You will get the crude. Normally crude doesn’t require to purify. Because it was almost 100% conversion.

[@sahanag3253]

tell the amine compound extraction procedure

[@Dr.Mosharraf]

Quench the reaction and then basify the liquid by using 1M NaOH or NaHCO3 solution to pH 8. Then extract with ethyl acetate. You can watch my extraction video.

[@RehanAnsari-bg9ut]

Sir plzz help me to convert 5 nitro salicylic acid to 5 amino salicylic acids sir its my m pharam project first step plz help to reduce nito grp 😢😢 plzz reply

[@Dr.Mosharraf]

I am extremely sorry I couldn’t reply earlier. I am at office now. I will reply very soon.

[@qwertyqwerty-cx8qn]

Nitro to amine amine to Nitro

[@Dr.Mosharraf]

I never did any reaction that gives amine to nitro.

[@qwertyqwerty-cx8qn]

@@Dr.Mosharraf probably for this you need a primary amine and some convenient, strong oxidizing agent. I think it's interesting.