Methyl p-toluenesulfonate → 7-Acetamido-1,4-dimethyl-1,8-naphthyridinium p-Toluenesulfonate

Participants

Reaction Steps

7-Acetamido-4-methyl-1,8-naphthyridine (13.3 g., 0.066 mole) was refluxed for 8 hours with 12.7 g. of methyl p-toluenesulfonate in 150 ml. of dry acetonitrile. The dark purple solution was cooled at 5° for several days; 21.8 g. (85%) of felted needles, m.p. 200°-202°, was removed. Addition of a large volume of ether to the mother liquors precipitated 2.3 g. (9%) more of the salt; m.p. 185°-190°. The 1H nmr was consistent with that expected for the desired product.

Provenance & Evidence