Hydrochloric Acid → HCID 19036721, compound

In 30 ml of pyridine was dissolved 3.00 g (11.3 mmol) of 4-(2-ethylhexyloxy)-2-hydroxybenzoic acid (compound 14), and 2.89 g (28.4 mmol) of acetic anhydride was added to the solution dropwise on an ice-water bath. After the dropwise addition, the mixture was stirred for 20 minutes, poured into 120 ml of a 12% aqueous solution of hydrochloric acid, and extracted with 150 ml of ethyl acetate. The organic layer was washed successively with three 150 ml portions of dilute hydrochloric acid, three 150 ml portions of water, and three 100 ml portions of a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by concentration. The resulting crude product was dissolved in 10 ml of methylene chloride, and a few drops of DMF were added thereto. To the mixture was further added dropwise 1.57 g (13.2 mmol) of methylene chloride at room temperature, followed by stirring for 15 minutes. The solvent was removed by distillation under reduced pressure, and the oily residue was dissolved in methylene chloride. The solution was added to 10 ml of a 70% aqueous solution of ethylamine on an ice bath. After the inner temperature was raised to room temperature, 300 ml of dilute hydrochloric acid was added thereto, and the mixture was extracted with 300 ml of ethyl acetate. The organic layer was washed successively with three 300 ml portions of water and two 300 ml portions of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated. The resulting crude product was recrystallized from hexane to obtain 2.06 g (62%) of N-ethyl-4-(2-ethylhexyloxy)-2-hydroxybenzamide represented by the following chemical formula (hereinafter referred to as compound 28) as white crystals. The analytical results are shown below. ##STR49##

1. additionwas added to the solution dropwise on an ice-water bath
2. additionAfter the dropwise addition
3. extractionextracted with 150 ml of ethyl acetate
4. washThe organic layer was washed successively with three 150 ml portions of dilute hydrochloric acid, three 150 ml portions of water, and three 100 ml portions of a saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationfollowed by concentration
7. dissolutionThe resulting crude product was dissolved in 10 ml of methylene chloride
8. additiona few drops of DMF were added
9. stirringby stirring for 15 minutes
10. customThe solvent was removed by distillation under reduced pressure
11. dissolutionthe oily residue was dissolved in methylene chloride
12. additionThe solution was added to 10 ml of a 70% aqueous solution of ethylamine on an ice bath
13. addition300 ml of dilute hydrochloric acid was added
14. extractionthe mixture was extracted with 300 ml of ethyl acetate
15. washThe organic layer was washed successively with three 300 ml portions of water and two 300 ml portions of a saturated sodium chloride aqueous solution
16. dry with materialdried over anhydrous sodium sulfate
17. concentrationconcentrated
18. customThe resulting crude product was recrystallized from hexane

ORD record

ord-e1887ae7b0db4fcda0e55bf65d2255f9

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646184