반응 #640586

반응 방정식

hydrochloric acid

2-Nitrobenzaldehyde

4-amino-2-methylbutanol

sodium borohydride

→

2-methyl-4-(2-nitrobenzylamino)butanol

수율 96.2%

용매

toluene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for two hours with Dean Stark dehydration apparatus
3. 3
   온도to cool
4. 4
   기타the solvent was evaporated under reduced pressure
5. 5
   농축The obtained concentrate
6. 6
   workup.DISSOLUTIONwas dissolved in methanol (100 ml)
7. 7
   workup.STIRRINGThe reaction mixture was further stirred at room temperature for two hours
8. 8
   기타the solvent was evaporated under reduced pressure
9. 9
   workup.ADDITIONWater (30 ml) was added
10. 10
    workup.DISSOLUTIONto dissolve the
11. 11
    농축concentrate
12. 12
    추출after extracted with ethyl acetate, pH
13. 13
    workup.ADDITIONby added a saturated sodium hydrogen carbonate aqueous solution
14. 14
    추출extracted with ethyl acetate
15. 15
    건조The organic layer was dried over anhydrous sodium sulfate
16. 16
    기타the solvent was evaporated under reduced pressure

실험 절차

2-Nitrobenzaldehyde (7.33 g, 48.5 mmol) and 4-amino-2-methylbutanol (5.00 g, 48.5 mmol) were dissolved in toluene (50 ml) and heated to reflux for two hours with Dean Stark dehydration apparatus. After allowed to cool, the solvent was evaporated under reduced pressure. The obtained concentrate was dissolved in methanol (100 ml), added with sodium borohydride (2.75 g, 72.8 mmol) under ice cooled condition and stirred at the same temperature for two hours. The reaction mixture was further stirred at room temperature for two hours, adjusted to pH 4 by adding 1N hydrochloric acid, and the solvent was evaporated under reduced pressure. Water (30 ml) was added to dissolve the concentrate and after extracted with ethyl acetate, pH was adjusted to 8 by added a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain 2-methyl-4-(2-nitrobenzylamino)butanol (11.12 g).

출처