13-05118. Isatide [Archived]

Nomenclature

CAS number: 464-73-3
1,1′,3,3′-Tetrahydro-3,3′-dihydroxy-[3,3′-bi-2H-indole]-2,2′-dione; 3,3′-dihydroxy-[3,3′-biindoline]-2,2′-dione; 3,3′-dihydroxy-3,3′-dihydroisoindigo; isatyde.
C16H12N2O4; mol wt 296.28.
C 64.86%, H 4.08%, N 9.46%, O 21.60%.

Description and references

Prepn by dimerization reduction of isatin with ammonium hydrosulfide: Laurent, Ann. Chim. 3, 372 (1841); by piperidine-catalyzed condensation of isatin and dioxindole: Heller, Ber. 37, 943 (1904); Wahl, Hansen, Compt. Rend. 178, 393 (1924); from isatin and acenaphthene in sunlight: Oliveri-Mandala, Deleo, Gazz. Chim. Ital. 79, 337 (1949). Structure: Lefèvre, Bull. Soc. Chim. Fr. 19, 113 (1916); Sumpter, J. Am. Chem. Soc. 54, 2917 (1932); Bergmann, ibid. 77, 1549 (1955).

Chemical structure

Properties

Prisms from alcohol or ether, dec 245°. Difficultly sol in alcohol and ether; practically insol in water.

Status

This monograph has been retired and is no longer subject to revision or update.