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Waffles SS
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My believe isnot murder of relatives and killing,..or anotherthing,please finish it.
I just love chemistry nothing else.
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ScienceSquirrel
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Mood: Dogs are pets but cats are little furry humans with four feet and self determination! 
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Really you would be better off just buying it as it is readily available.
Otherwise the way to go is via some of the routes in the discussion section in the preparation below, assuming that you don't have an autoclave handy
http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV5...
[Edited on 22-12-2009 by ScienceSquirrel]
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Polverone
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Quote: Originally posted by Waffles SS  | My believe isnot murder of relatives and killing,..or anotherthing,please finish it.
I just love chemistry nothing else. |
I have done you a favor by renaming your account so that any future technical questions of yours can be discussed without distraction.
PGP Key and corresponding e-mail address
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Satan
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| Quote: Originally posted by not_important |
The Fischer synthesis can be used to directly produce IIA and IBA or simple derivatives of them, without going through indole in an intermediate step.
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For what derivatives of indole this reaction will also work? Or in other words, wich functional groups would not interfere with normal progres of
Fischer synthesis?
[Edited on 22-12-2009 by Satan]
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sonogashira
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It is acid-catalysed reaction, so anything resistant to decoposition by acid (amines, carboxylic acids etc.) is ok I think.
[And maybe, if 'WaffenSS' is changed, 'Satan' is as big a enemy?! Or the only enemy, to some! Hehe!]
[Edited on 22-12-2009 by sonogashira]
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ChrisWhewell
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What do you intend to do with indole ?
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hector2000
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| Quote: Originally posted by Waffles SS | I have problem with Fischer indole synthesis For making IAA.
@Nicodem said this reaction need special condition and he suggest Phenylhydrazone+Pyruvic acid but i need more detail about it.
Anyone can send refrence or instruction about that? |
here you are
us2,701,250
process of producing indole3-acetic acid by fischer method
Attachment: US2701250.pdf (237kB)
This file has been downloaded 1015 times
Chemistry=Chem+ is+ Try
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Satan
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Another document about IAA:
Attachment: Synthesis.Indoleacetic.Acids.Glutamine.pdf (279kB)
This file has been downloaded 1337 times
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JohnWW
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That reminds, me, "Satan": how do Satanists celebrate Christmas? With horns, hooves, a pointed tail, the wings of a bat, goatee beard, red scaly skin,
smelling of sulfur (or of selenium or tellurium or polonium, or of indole, if you like), and going around dressed in red tights and brandishing a
pitchfork, it must be rather difficult.
Another indole derivative is the purple dye "Tyrian purple", used to dye the robes of Roman Emperors and patricians, originally obtained from two
species of whelk, originally called Murex brandaris and Murex trunculus, which are the older names for Haustellum brandaris and Hexaplex trunculus,
found in the Mediterranean, in what was a very smelly and costly operation; see http://en.wikipedia.org/wiki/Tyrian_purple . Fortunately the stuff can now be made synthetically. It is 6, 6'-dibromoindigo, a double-bonded dimer
of indole via the 5-membered rings, on which there are also keto groups, and there are Br atoms on the aromatic rings.
There is also the important dye indigo, also a substituted dimer via the 5-membered rings of indole, see http://en.wikipedia.org/wiki/Indigo_dye . It was originally obtained from the indigo plant, and is now produced synthetically in large amounts,
although not via indole itself.
[Edited on 25-12-09 by JohnWW]
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Vogelzang
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US 3790596 METHOD OF PRODUCING INDOLE AND SUBSTITUTION PRODUCTS OF THE SAME
acetaldehyde phenylhydrazone -> indole
US 3847937 PROCESS FOR THE PREPARATION OF INDOLES
diphenylaminoethane (from aniline and acetaldehyde) -> indole
Also found during the search:
US 2159167 Alcoholic beverage of reduced inebriating capacity
pyruvic acid:
http://www.sciencemadness.org/talk/viewthread.php?tid=8481
[Edited on 24-12-2009 by Vogelzang]
[Edited on 24-12-2009 by Vogelzang]
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Vogelzang
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US 1891057 Production of indole and derivatives thereof
US 2086805 Purification of the isatins
US 2307244 Production of indoles
Page 1 column 1 lines 10+:
It has been proposed to produce indole from indigo by a preliminary reduction with tin and hydrochloric acid followed by destructive reduction with
zinc dust at distillation
temperatures. It has also been proposed to produce indole by the distillation of indigo with the aluminum powder at red heat.
US 2365966 Production of indole -> in German Patent No. 260,327 it, is
disclosed that indole may be formed by heating an aqueous solution of indoxyl
and an alkali metal hydroxide in an autoclave to a temperature above 200' C.
US 1657869 Process for producing indigo white
US 1721319 Zn+2NaHSO3=2H+ZnSO3+Na2SO3 ; can be used to reduce indigo to indigo white
US 2130878 Leucoindigo
US 2159930 Preparation of leuco-indigo
US 1588960 Indigo dyestuff
shows structures of indole, indoxyl, isatin, etc.
US 2017120 Production of discharge effects
Page 1 column 2 lines12+:
The zinc compounds of leuco vat dyestuffs have been found particularly convenient for
application in accordance with the present invention, but other insoluble metal compounds may be utilized if desired, for example compounds with
cadmium, aluminium, tin, lead or iron. These insoluble metal compounds of leuco vat dyestuffs are conveniently prepared by interaction between the
alkali metal salts of the leuco compounds and appropriate metal salts, preferably such as are water-soluble. For instance, the dyestuff in question
may be vatted with sodium hyrosulphite or other
reducing agent and just sufficient caustic alkali to yield a solution of the
leuco compound. The solution thus obtained, if desired after filtration,
may be treated with an aqueous solution of the appropriate metal salt, for
example a concentrated solution of zinc chloride, whereby the desired metal
compound of the leuco vat dyestuff may be precipitated.
US 3118724 Processes for reduction of organic substances with alkali-metal borohydrides in the presence of catalysts
US 5350425 Method of reducing vat dyes and the process of dyeing fabrics therein
column 1 lines 49+
Typically, sodium dithionite has been employed to reduce the dyes to
their leuco form, as is shown U.S. Pat. No. 3,798,172. Sodium dithionite
decomposes rapidly in the presence or absence of air; therefore, large, excess
quantities of this compound are used to reduce all of the dye and to maintain
the dye in is soluble leuco form. Regrettably, the use of sodium dithionite
raises ecological concerns.
column 1 lines 64+
Another reducing agent that has received some attention is
thiourea dioxide in an alkaline solution. However, thiourea dioxide is a
strong reducing agent, and therefore tends to over reduce the vat dye. When
reducing indigo overreduction is readily apparent by the smell of fecal
material which is present when indole (the overreduction product) is in the
reaction.
indigo -> leucoindigo using Al, NaOH & H2O column 7, several examples columns 8 and 9
US 2872482 Process of making thiourea dioxide
Column 1
Thiourea dioxide has heretofore been prepared by the oxidation of thiourea by the use of hydrogen peroxide.
US 2150921 Manufacture of imino-amino-methane-sulphinic acid
oxidation of thiourea by the use of hydrogen peroxide
US 2164930 Process for reducing vat dyestuffs
use of thiourea dioxide for reducing vat dyes
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unome
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Attached find a review of the Fischer Indole synthesis.
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Waffles SS
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Thanks @VogelZang and Hector,
@JohnWW now i am Waffles SS,this remind you another thing again?
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Vogelzang
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Ye Ol' zinc dust distillation to remove oxygen atoms.
Indole chemistry began to develop with the study of the dye indigo. Indigo can be converted to isatin and then to oxindole. Then, in 1866, Adolf von
Baeyer reduced oxindole to indole using zinc dust.[2] In 1869, he proposed a formula for indole (left).[3]
2. Baeyer, A. (1866). "Ueber die Reduction aromatischer Verbindungen mittelst Zinkstaub". Ann. 140: 295. doi:10.1002/jlac.18661400306.
3. Baeyer, A.; Emmerling, A. (1869). "Synthese des Indols". Chemische Berichte 2: 679. doi:10.1002/cber.186900201268.
http://en.wikipedia.org/wiki/Indole
[Edited on 25-12-2009 by Vogelzang]
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Vogelzang
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This discusses the production of indole from pyrrole (page 629).
http://books.google.com/books?id=MAA5AAAAIAAJ&pg=RA1-PA6...
[Edited on 25-12-2009 by Vogelzang]
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Satan
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How would react hydrazone, made from condensation of 4-methoxyphenylhydrazine and acetaldehyde? There are two possible reaction products,
5-methoxyindole and 6-methoxyindole. My true question is: how to predict how substitiued phenylhydrazones would cyclicyze?
From 5-methoxyindole, melatonin can be made, it would be interesting synthesis of human hormone.
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sonogashira
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| Quote: Originally posted by Satan | | From 5-methoxyindole, melatonin can be made, it would be interesting synthesis of human hormone. |
If it is your interest there is this thread by a person now-departed from this site, God bless him Lot of good alternative methods and (maybe!) even the one you have an interest in...
http://www.sciencemadness.org/talk/viewthread.php?tid=10120
[Edited on 26-12-2009 by sonogashira]
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Vogelzang
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US patents which disclose processes for producing indoles from phenylhydrazones: 4965369, 5229413, 2995566, 1866956, 2057948, 2068800, 3557142.
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Vogelzang
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Another US patent on IAA 2701251.
US patents on anilines + glycols -> indoles: 4436916, 4436917, 4443615, 4456760, 4473698, 4474969, 4476310, 4659841, 4727161, 4732654, 4831158,
4937353, 5175308, 4404063 (with indole separation).
An interesting tryptamine process: US 5037845
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unome
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Damn, I thought my attachment attached, obviously not here tis again...
B. Robinson, The Fischer Indole Synthesis, Chem. Rev., 1963, 63 (4), pp 373–401 (DOI: 10.1021/cr60224a003)
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Rattata2
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I like this idea:
React benzaldehyde with nitroethane forming a beta-nitrostyrene. Nitrate this with HNO3 - this should nitrate mostly ortho-. Follow by heating with
iron turnings to form indole.
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unome
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Why aren't the attachments working?
There should be 4 attached here NOW
Attachment: VanOrder.Lindwall.Chem.Review.Indole.pdf (306kB)
This file has been downloaded 1669 times
Attachment: Bidylo.Yurovskaya.Synthesis.Tryptamines.Latent.AminoButanal.Review.pdf (835kB)
This file has been downloaded 8660 times
Attachment: indole.synth.review.1994-99.pdf (791kB)
This file has been downloaded 2785 times
Attachment: Improved.Synthesis.DMT.Psilocin.pdf (1.4MB)
This file has been downloaded 1332 times
[Edited on 15-1-2010 by unome]
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Rattata2
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Whoops I meant nitrom*ethane in the previous post. My bad, makes things easier eh? :p
Anyways, I found this recently which to me looks like an exciting method of indole synthesis: http://www.sciencedirect.com/science?_ob=ArticleURL&_udi...
I can't access the paper myself (anyone who can if you wanna upload it thatd be great) but the abstract says wonders..it's a fischer indole synthesis
using pyruvic acid as the ketone, under microwave irradiation (with ZnCl2 as a catalyst.) This would first form indole-2-carboxylic acid as an
intermediate which would then be decarboxylated to yield indole. Apparently in a microwave, this whole procedure can be done in a one-pot synthesis
Not sure if the PCl5 is really required for this (it isn't for classical fischer indole synthesis is it?), but I do believe the reaction is supposed
to take place in acidic conditions. Anyways hope this turns out useful to someone
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IPN
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Here is the full paper.
Attachment: A new and efficient one-pot synthesis of indoles.pdf (95kB)
This file has been downloaded 2830 times
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Waffles SS
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One funny question:
May we use kitchen microwave oven for microwave irradiation step?
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