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Topic: 5-amino-1-naphthol Synthesis Opinion  (Read 5449 times)

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Offline tallec01

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5-amino-1-naphthol Synthesis Opinion
« on: August 01, 2012, 04:42:04 PM »
Quickest route to 5-amino-1-naphthol anyone?

Offline Dan

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #1 on: August 01, 2012, 07:49:39 PM »
It's commercially available, buying it would be the easiest option.
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Offline tallec01

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #2 on: August 02, 2012, 02:17:52 PM »
Fully aware...just curious about the chemistry used to make it. Some sort of condensation involved?

Offline camptzak

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #3 on: August 03, 2012, 02:34:59 AM »
whats available as starting materials?

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Offline tallec01

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #4 on: August 03, 2012, 11:31:41 AM »
Lets say 1-naphthol or 1-naphthylamine. How would you introduce the other functionality at the 5 position?

Offline camptzak

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #5 on: August 03, 2012, 12:53:28 PM »
ok well if you were to start with 1-napthylamine you could chlorinate the rings with iron chloride and chlorine gas and then use nucleophilic aromatic substitution to replace the chlorine with a hydroxyl group.
The amine is an activating substituent so you would get chlorine at the 5 position on some rings and at other positions at other rings. So you would have to seperate your desired compounds before hitting it with sodium hydroxide.

If you were to start with 1-napthol you could use sulfuric acid and nitric acid to nitrate the ring. the hydroxyl group is also activating so again you would get nitration at the 5 position as well as other positions and you would have to sperate your desired compound.
you would then have to reduce your nitrated ring to get your amine.

If you are actualy planning on carrying this out then try to start with the amine and add the OH group. That would be the easiest way. I would not actually attempt the nitration pathway.
"Chance favors the prepared mind"
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Offline orgopete

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #6 on: August 04, 2012, 08:11:15 AM »
If you nitrate 1- or 2-naphol, what is the product? Isn't this a general result from all activating groups? What is the product for the dinitration of naphthalene?
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Offline camptzak

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #7 on: August 05, 2012, 01:29:46 AM »
doesnt the ring undergo addition by the nitrates? at the positions that are allowded by the activating oH?
"Chance favors the prepared mind"
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Offline AWK

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #8 on: August 05, 2012, 02:35:00 AM »
synthesis
Yakugaku Zasshi. 1976 Oct;96(10):1259-64
AWK

Offline orgopete

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #9 on: August 05, 2012, 07:33:53 AM »
doesnt the ring undergo addition by the nitrates? at the positions that are allowded by the activating oH?

Correct. If you start with 1-naphthol, you will get a mixture of 2-, 4-nitro, and 2,4-dinitro-1-naphthol because the OH is activating. Nitration occurs in the ring containing an activating group.

If you start with 1-nitronaphthalene, nitration occurs in the not deactivated ring and you will get 1,5- and 1,8-dinitronaphthalene. If you start with the naphthalenium salt (C10H7NH3+) of 1-aminonaphthalene, what product would you predict? (I am thinking hypothetically as I am uncertain of the effectiveness of a naphthalenium salt as a meta director. Anilinium salts may still give some o/p products, as I recall.)

AWK, the reference would be good if I had access to it, but in my case, it will take a week or so to order from the interlibrary loan.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline AWK

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #10 on: August 05, 2012, 08:05:41 AM »
AWK, the reference would be good if I had access to it, but in my case, it will take a week or so to order from the interlibrary loan.
It concerns of synthesis through 1,5-dinitro derivative. After selective reduction (with sulfides) they use Fremy's salt - diazotization removes NH2 completely!).
Nitration of 1-naphtylamine gives mixture 1,5 and 1,8 isomers.
« Last Edit: August 05, 2012, 08:31:54 AM by AWK »
AWK

Offline camptzak

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Re: 5-amino-1-naphthol Synthesis Opinion
« Reply #11 on: August 05, 2012, 02:21:59 PM »
well im sorry for the bad advice then!
I drew it out and found that when i attacked the ring with the NO2 at the 5 position I resonated the charge and found the cation under the OH. I must have drawn it incorrectly, I will go back and do it again.
"Chance favors the prepared mind"
-Louis Pasteur

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