Stollé synthesis
Encyclopedia
The Stollé synthesis is a series of chemical reaction
s that produce oxindole
s from aniline
s and α-haloacid chlorides (or oxalyl chloride
).
The first step is an amide
coupling, while the second step is a Friedel-Crafts reaction
. An improved procedure has been developed.
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
s that produce oxindole
Oxindole
Oxindole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring...
s from aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
s and α-haloacid chlorides (or oxalyl chloride
Oxalyl chloride
Oxalyl chloride or ethanedioyl dichloride is a chemical compound with the formula 2. This colourless, sharp-smelling liquid, the diacid chloride of oxalic acid, is a useful reagent in organic synthesis...
).
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
coupling, while the second step is a Friedel-Crafts reaction
Friedel-Crafts reaction
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel–Crafts reactions: alkylation reactions and acylation reactions. This reaction type is a form of electrophilic aromatic substitution...
. An improved procedure has been developed.