Sciencemadness Discussion Board

skatole conversion into indole

nikotyna1939 - 28-11-2018 at 19:08

is it possible to convert skatole to indole
if you know can you show the way

12thealchemist - 29-11-2018 at 03:32

You would want to protect the nitrogen of the ring, then probably oxidise the methyl to a carboxylate group, then perform a decarboxylation, followed by deprotection of the nitrogen. That would be my guess. You would want to pick a protecting group that would be immune to whatever oxidant you use on the methyl.

CuReUS - 29-11-2018 at 06:13

1.Convert skatole to indole -3 carboxylic acid -https://onlinelibrary.wiley.com/doi/10.1002/cber.18880210137...

2.decarboxylate to indole by heating at 230'C -https://onlinelibrary.wiley.com/doi/abs/10.1002/cber.1897030...

its a 1 pot procedure :P

Convert skatole to indole -3 carboxylic acid

nikotyna1939 - 5-12-2018 at 17:08

can anybody knows the steps to Convert skatole to indole -3 carboxylic acid

UC235 - 5-12-2018 at 17:38

Quote: Originally posted by CuReUS  
1.Convert skatole to indole -3 carboxylic acid -https://onlinelibrary.wiley.com/doi/10.1002/cber.18880210137...

2.decarboxylate to indole by heating at 230'C -https://onlinelibrary.wiley.com/doi/abs/10.1002/cber.1897030...

its a 1 pot procedure :P


The decarboxylation is likely catalyzed by copper, since the indole should provide the essential ligand in the same way nicotinic acid does. I'd toss in some copper chromite.

diddi - 5-12-2018 at 17:40

thats some might smelly chemistry :)

Assured Fish - 6-12-2018 at 22:00

@nikotyna1939
Im not sure if your merely posing the question for curiosity sake or if you intend on putting this to practice.
If the later is the case, where on earth did you acquire your skatole from. The stuff is hellishly expensive from most suppliers who have the balls to sell it and i cannot imagine you made it yourself (although NileRed does have a detailed video on it).
Unless of coarse you extracted it :o

nikotyna1939 - 7-12-2018 at 20:42

Quote: Originally posted by nikotyna1939  
is it possible to convert skatole to indole
if you know can you show the steps in detail

just curious

nikotyna1939 - 8-12-2018 at 23:24

i wondered and skatole is cheaper in my country. also i needed indole for making Indole-3-butyric acid

[Edited on 9-12-2018 by nikotyna1939]