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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: littlejoker on October 17, 2015, 12:16:26 PM

Title: Convert 2,6-dimethylphenol into 2,6-dimethylaniline
Post by: littlejoker on October 17, 2015, 12:16:26 PM

I'm having to write the synthesis of Lidocaine, starting with 2,6-dimethylphenol and fewer-than-four-carbon compounds, and I know we must somehow convert that into 2,6-dimethylaniline. Steps after that seem quite easy and they are mentioned everywhere but this step is quite difficult to me.
I'm thinking if we can treat 2,6-dimethylphenol with HNO3/H2SO4 to form a -NO2 group at the para place to -OH and then convert -OH into OMs and use NH3 to replace -OMs with -NH2. Can it be possible?

Title: Re: Convert 2,6-dimethylphenol into 2,6-dimethylaniline
Post by: sjb on October 17, 2015, 04:01:00 PM

Quote from: littlejoker on October 17, 2015, 12:16:26 PM

I'm having to write the synthesis of Lidocaine, starting with 2,6-dimethylphenol and fewer-than-four-carbon compounds, and I know we must somehow convert that into 2,6-dimethylaniline. Steps after that seem quite easy and they are mentioned everywhere but this step is quite difficult to me.
I'm thinking if we can treat 2,6-dimethylphenol with HNO₃/H₂SO₄ to form a -NO₂ group at the para place to -OH and then convert -OH into OMs and use NH₃ to replace -OMs with -NH2. Can it be possible?

Is nucleophilic substitution usual at aromatic centres? I think conversion to the mesylate is a good plan, though. There may be other ways to add the nitrogen - I'm not sure that nitration is the way to go (how do you intend removing it?)

Title: Re: Convert 2,6-dimethylphenol into 2,6-dimethylaniline
Post by: littlejoker on October 23, 2015, 05:15:49 AM

I'm so sorry for being gone for a few days...

Well, it's a little difficult to ged rid of -NO2 so can we use -SO3H instead?