phenyl anthranilate

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Terry Rankine - 03 Sep 2003 13:58 GMT

Just to make life hard:
I need to synthisize about 5g of phenyl anthranilate for a uni lab
project.
Can some one please check or comment on this method our group came up
with.

start with
anthranilic acid (cas 118-92-3) and add conc H+ to protonate the amine
group.
then SOCl2 (thionyl chloride) to create the acid chloride
then add phenol in CH2Cl2 (dicloromethane)
reflux for a bit
and hopefuly a yeild of phenyl anthranilate.

Some questions:
what starting ratios of reactants should i use? which one should be in
excess?
has anyone done it before? and aryl sub on a anthranilic acid?
I am limited on starting materials - common stuff only. Is there any
other common starting materials i could use - did i over look
something?

I am eagerly awating a reply
Thankyou
Terry Rankine

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

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Uncle Al - 05 Sep 2003 19:44 GMT

> Just to make life hard:
> I need to synthisize about 5g of phenyl anthranilate for a uni lab
[quoted text clipped - 17 lines]
> other common starting materials i could use - did i over look
> something?

What makes you think that unprotonated product will sit around rather
than react with itself?

You will probably need *one* equivalent of a very mild acid scavanger
to form the phenyl ester from the protonated acid chloride - and it
must be separable afterward. Dimethylaniline won't do it. Maybe
powdered calcium carbonate or even Na2SO4 (anh); or an anhydrous weak
cation exchange resin. I tend more toward stir overnight than reflux
it to death unless rt won't drive it. Do it dry and under inert gas.
Make certain your phenol is clean white, or distill it (and rigorously
avoid skin contact).

Normally the phenol would be taken in excess. If so, how will your
remove the unreacted stuff?

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Uncle Al
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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

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Muhammar - 09 Sep 2003 18:15 GMT

Make o-nitrobenzoyl chloride (from o-nitrobenzoic acid, oxaloyl
chloride and
1 drop of DMF at R.T.).
Treat it with phenol in presence of pyridine, do acidic work-up.
Take the formed phenyl o-nitrobenzoate and hydrogenate the sucker in
THF (or benzene or EtOAc or dioxane) in presence of anhydrous HCl
(from HCl-dioxane solution, for example). Use Pd-C {but not Pt or
Raney Ni} at 1 atm of H2.
Your product will precipitate as hydrochloride - filter it together
with catalyst, suspend the sludge in aceton, filter off the catalyst
and evaporate the acetone supernatant.

You should have your product as solid hydrochloride. The free base
will not
be very stable.

Do only at your own risk. Also, check Beilstein. I bet someone made
this material before.

> Just to make life hard:
> I need to synthisize about 5g of phenyl anthranilate for a uni lab
> project.
> Can some one please check or comment on this method our group came up
> with.

> start with
> anthranilic acid (cas 118-92-3) and add conc H+ to protonate the amine
[quoted text clipped - 3 lines]
> reflux for a bit
> and hopefuly a yeild of phenyl anthranilate.

> Some questions:
> what starting ratios of reactants should i use? which one should be in
[quoted text clipped - 3 lines]
> other common starting materials i could use - did i over look
> something?

> I am eagerly awating a reply
> Thankyou
> Terry Rankine

Signature

Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

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Natural Science Forum / Chemistry / Organic Synthesis / September 2003

phenyl anthranilate