반응 #1504768

반응 방정식

methyl 4-azidomethylsalicylate

hydrochloric acid

hydrogen

→

methyl 4-aminomethylsalicylate hydrochloride

수율 65.0%

용매

ethanol

methanol

water

반응 조건

후처리

1. 1
   여과The reaction mixture was then filtered through a 0.45 mm nylon
2. 2
   여과filter
3. 3
   세척The retained solid was then washed with methanol (150 mL), water (100 mL), and methanol again (150 mL)
4. 4
   기타The combined filtrates were evaporated to dryness
5. 5
   기타to afford a tan solid
6. 6
   기타White crystals formed quickly
7. 7
   온도Finally, the mixture was then chilled for 16-18 hours at 4° C.
8. 8
   기타crystallization
9. 9
   여과The solid was filtered
10. 10
    세척washed with a little cold ethanol (50 mL)
11. 11
    건조diethyl ether (150 mL), and dried in vacuo over potassium hydroxide pellets

실험 절차

Crude methyl 4-azidomethylsalicylate was dissolved in methanol (750 mL) in a 2 L Parr hydrogenation flask. Palladium on carbon catalyst (10% [w/w], 3.8 g) in water (25 mL) was added, followed by concentrated hydrochloric acid (35 mL). The flask was affixed to a Parr hydrogenator, and the mixture was shaken at room temperature under 40 psi of hydrogen for 16 hours. The reaction mixture was then filtered through a 0.45 mm nylon filter. The retained solid was then washed with methanol (150 mL), water (100 mL), and methanol again (150 mL). The combined filtrates were evaporated to dryness to afford a tan solid. This solid was dissolved in hot denatured ethanol (150 mL) and the solution was allowed to cool to room temperature. White crystals formed quickly. Finally, the mixture was then chilled for 16-18 hours at 4° C. to complete crystallization. The solid was filtered, washed with a little cold ethanol (50 mL) and then diethyl ether (150 mL), and dried in vacuo over potassium hydroxide pellets to afford 51.5 g (65% yield based on methyl 4-bromomethylsalicylate) of methyl 4-aminomethylsalicylate hydrochloride (m.p. 225°-227° C., open capillary, uncorrected).

출처