Hydrochloric Acid → N-(2-hydroxyethyl)-2-methoxy-1-naphthamide

Temperature

0 °C

A solution of 2-methoxy-naphthalene-1-carboxylic acid (0.50 g, 2.5 mmol) in anhydrous dichloromethane at 0° C. was treated dropwise with a 2.0 M solution of oxalyl chloride in dichloromethane (1.9 mL, 3.8 mmol). The resulting solution was stirred under a N2 atmosphere at 0° C. for 20 min, then allowed to warm to r.t. and stirred 1 hr. The solution was cooled to 0° C., and ethanolamine (0.3 mL, 5.0 mmol) and triethylamine (1.0 mL, 7.2 mmol) were added. The resulting mixture was stirred at 0° C. for 15 min, then allowed to warm to r.t. and stirred 90 min. The mixture was poured into 1N HCl (20 mL) and extracted with dichloromethane (2×20 mL), and the combined organic layers were washed with saturated NaHCO3 (20 mL) and dried over Na2SO4. The drying agent was filtered off, and the solvent was removed in vacuo to give the title compound as colorless syrup.

1. temperatureto warm to r.t.
2. stirringstirred 1 hr
3. temperatureThe solution was cooled to 0° C.
4. stirringThe resulting mixture was stirred at 0° C. for 15 min
5. temperatureto warm to r.t.
6. stirringstirred 90 min
7. extractionextracted with dichloromethane (2×20 mL)
8. washthe combined organic layers were washed with saturated NaHCO3 (20 mL)
9. dry with materialdried over Na2SO4
10. filtrationThe drying agent was filtered off
11. customthe solvent was removed in vacuo

ORD record

ord-86cf4e79dd2341388d0116b27c27d9df

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378414B2