Hydrochloric Acid → HCID 57682764, compound

1.20 g of 3-allyl-4-methoxy-2-(methoxymethoxy)benzoic acid was dissolved in 15 ml of anhydrous tetrahydrofuran, and 0.84 g of 1,1′-carbonyldiimidazole was then added thereto. The obtained mixture was stirred at room temperature under nitrogen atmosphere for 25 minutes. Thereafter, 11.8 ml of methylamine (a 2.0 M tetrahydrofuran solution) was added to the reaction solution, and the obtained mixture was then stirred at room temperature for approximately 5 hours. Thereafter, the reaction mixture was cooled on ice, and 2.5 ml of concentrated hydrochloric acid was added thereto. The obtained mixture was stirred at room temperature for 15 minutes. The reaction solution was extracted with ethyl acetate. The organic layer was washed with water 3 times and then washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride solution. The resultant product was then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. 20 ml of anhydrous tetrahydrofuran was added to the obtained residue, and then, 1.53 g of 1,1′-carbonyldiimidazole was added thereto. The reaction mixture was heated to reflux under nitrogen atmosphere for approximately 2 hours. The reaction solution was cooled to a room temperature, and the solvent was then removed under a reduced pressure. Ethyl acetate and water were added to the residue, so as to separate an organic layer. The obtained organic layer was washed with water twice and then with a saturated sodium chloride solution. The resultant product was then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was reprecipitated from ethyl acetate-n-hexane, so as to obtain 0.97 g of the subject compound.

1. stirringthe obtained mixture was then stirred at room temperature for approximately 5 hours
2. additionwas added
3. stirringThe obtained mixture was stirred at room temperature for 15 minutes
4. extractionThe reaction solution was extracted with ethyl acetate
5. washThe organic layer was washed with water 3 times
6. washwashed with a saturated sodium bicarbonate aqueous solution
7. dry with materialThe resultant product was then dried over anhydrous magnesium sulfate
8. customAfter removing the drying agent
9. filtrationby filtration
10. concentrationthe organic layer was concentrated under a reduced pressure
11. addition20 ml of anhydrous tetrahydrofuran was added to the obtained residue
12. addition1.53 g of 1,1′-carbonyldiimidazole was added
13. temperatureThe reaction mixture was heated
14. temperatureto reflux under nitrogen atmosphere for approximately 2 hours
15. temperatureThe reaction solution was cooled to a room temperature
16. customthe solvent was then removed under a reduced pressure
17. additionEthyl acetate and water were added to the residue
18. customso as to separate an organic layer
19. washThe obtained organic layer was washed with water twice
20. dry with materialThe resultant product was then dried over anhydrous magnesium sulfate
21. customAfter removing the drying agent
22. filtrationby filtration
23. concentrationthe organic layer was concentrated under a reduced pressure
24. customThe residue was reprecipitated from ethyl acetate-n-hexane

ORD record

ord-62b4cb5bbb6046c6a26a42b3df670b7d

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2