Hydrochloric Acid → Methyl 4-[(2-propynylamino)carbonyl]benzoate

Terephthalic acid mono methyl ester (0.775 g) was dissolved in dry pyridine (10 ml) in a N2 atmosphere. The solution was cooled in an ice-water bath, and thionyl chloride (0.44 ml) was added dropwise. The mixture was warmed to room temperature and was stirred for 1 h to give a pale brown suspension. The mixture was re-cooled in an ice-water bath, and a suspension of proparglyamine hydrochloride (413 mg) in pyridine was added rapidly. The mixture was warmed to room temperature and was stirred for 18 h to give a dark solution. The solvent was evaporated in vacuo to give a dark brown gum, which was dissolved in Ea/hexane/acetic acid (1:1:1% v/v) and flash chromatographed using the same solvent system to give a yellow sludge, which was triturated with ER to give the title compound as a white solid, (0.544 g), m.p. 151.5°-153°.

1. temperatureThe solution was cooled in an ice-water bath
2. customto give a pale brown suspension
3. temperatureThe mixture was re-cooled in an ice-water bath
4. additionwas added rapidly
5. temperatureThe mixture was warmed to room temperature
6. stirringwas stirred for 18 h
7. customto give a dark solution
8. customThe solvent was evaporated in vacuo
9. customto give a dark brown gum, which
10. custom1% v/v) and flash chromatographed
11. customto give a yellow sludge, which
12. customwas triturated with ER

ORD record

ord-43046e9f1eb749a095a56f4ec37d9ce6

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04855314