Methyl 3-methylanthranilate → HCID 14155300, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-methylanthranilate (2.1 g, 13 mmol) was dissolved in 4 ml pyridine and 6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After a mild exothermic reaction subsided the reaction mixture was stirred at 50° C. for 24 hours. The pyridine was removed by evaporation at reduced pressure and the residue was treated with in 10% aqueous sodium bicarbonate. Insoluble material was collected by filtration, washed with ether and dried to yield 2.9 (63%) of the desired product as a solid, mp 198.5°-205° C. An analytical sample was prepared by recrystallization from ethanol to yield a crystalline solid, mp 208.5°-210.5° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Provenance & Evidence