Stollé synthesis explained

The Stollé synthesis is a series of chemical reactions that produce oxindoles from anilines and α-haloacid chlorides (or oxalyl chloride).^{[1] [2] [3] [4]}

The first step is an amide coupling, while the second step is a Friedel–Crafts reaction.^{[5] [6]} An improved procedure has been developed.^[7]

See also

• Indole
• Hinsberg oxindole synthesis

Notes and References

1. Stollé. R.. Ber.. 1913. 46. 3. 3915–3916. 10.1002/cber.191304603186. Über eine neue Methode zur Darstellung N-substituierter Isatine. (Vorläufige Mitteilung). German.
2. Stollé. R.. Ber.. 1914. 47. 2. 2120–2122. 10.1002/cber.191404702112. Über Phenyl-oxindol. German.
3. Stollé. R.. R.. Bergdoll. M.. Luther. A.. Auerhahn. W.. Wacker. J. Prakt. Chem.. 1922. 105. 1. 137–148. 10.1002/prac.19221050111. Über N-substituierte Oxindole und Isatine. German.
4. Stollé. R.. R.. Bergdoll. M.. Luther. J. Prakt. Chem.. A.. Auerhahn. W.. Wacker. 1930. 128. 1. 1–43. Über N-substituierte Oxindole und Isatine. German. 10.1002/prac.19301280101.
5. Sumpter. Ward C.. Chem. Rev.. 1944. 34. 393–434. 10.1021/cr60109a003. The Chemistry of Isatin. 3.
6. Sumpter. Ward C.. Chem. Rev.. 1945. 37. 443–479. 10.1021/cr60118a003. The Chemistry of Oxindole. 3. 21013427.
7. Percy L.. Julian. Josef. Pikl. J. Am. Chem. Soc.. 1935. 57. 563–566. 10.1021/ja01306a053. Studies in the Indole Series. IV. The Synthesis of d,l-Eserethole. 3.