2-Methylbenzamide (o-Toluamide) has been used in total synthesis of phenolic protoberberine alkaloid, cerasonine.
Organic Syntheses, Coll. Vol. 2, p. 586, 1943
The Journal of Organic Chemistry, 57, p. 2700, 1992
DOI: 10.1021/jo00035a030
O-TOLUAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
ACUTE/CHRONIC HAZARDS: O-TOLUAMIDE may react violently if exposed to open flame; it should be isolated from all sources of ignition.
Flash point data for O-TOLUAMIDE are not available, however O-TOLUAMIDE is probably combustible.
Crystallise o-toluamide from hot water (10mL/g) and dry in air. [Noller Org Synth Coll Vol II 586 1943, Beilstein 9 H 465, 9 II 319, 9 III 2304.]
