Some examples of the Schmidt rearrangement was written by Edwards, W. G. H.;Petrow, V.. And the article was included in Journal of the Chemical Society in 1948.Safety of 6-Chloro-2-aminobenzamide This article mentions the following:
The Schmidt rearrangement is carried out in 10 volumes concentrated H2SO4 at 0° by adding dropwise 1.1 equivalents NaN3 in a min. quantity of H2O and allowing the mixture to stand overnight. Isatin (I) gives ο-H2NC6H4CONH2 (II); the 5-NO2 derivative of II results in 42% yield; the 6-Cl derivative of I gives 80% of the 4-Cl derivative of II; the 4-Cl derivative of I gives 40% 6,2-Cl(H2N)C6H3CO2H. Isatin-7-carboxylic acid fails to react, as do oxindole and its N-HO and 5-NO2 derivatives 1-Acetylindoxyl gives a dark amorphous solid which could not be purified. Benzisoxazolone & and coumaranone are recovered unchanged. Acenaphthenone gives a tarry product that could not be purified. Acenaphthenequinone gives naphthalic anhydride. 3-Acetylacenaphthene gives a mixture of 3-aminoacenaphthenesulfonic acid and the Ac derivative; the latter forms an S-benzylisothiuronium salt, m. 226° (decomposition, corrected); in H3PO4, unchanged ketone was recovered. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Safety of 6-Chloro-2-aminobenzamide).
6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Safety of 6-Chloro-2-aminobenzamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics