반응 #53540

반응 방정식

ammonium sulfate

quinaldine

sulfuric acid

methanol

→

2-methyl-4-hydroxymethylquinoline

수율 27.0%

용매

water

반응 조건

후처리

1. 1
   기타Nitrogen was bubbled into the solution for 20 min
2. 2
   기타quenched with 10% sodium hydroxide (pH=9-10)
3. 3
   기타Methanol was removed by concentration in vacuo
4. 4
   추출the resulting aqueous solution was extracted with ethyl acetate three times
5. 5
   여과The combined organic phase was filtered through silica gel
6. 6
   세척washed with water and brine
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated
9. 9
   기타Crystallization from ethyl acetate

실험 절차

To a solution of quinaldine (75 g, 0.523 mol) in methanol (1100 mL) and water (550 mL) at room temperature was added sulfuric acid (28 mL, 0.523 mol) followed by iron(II) sulfate heptahydrate. Nitrogen was bubbled into the solution for 20 min and ammonium sulfate (177 g, 1.56 mol) was added. The resultant mixture was stirred in a water bath (20° C.) under nitrogen for 4 hours and quenched with 10% sodium hydroxide (pH=9-10). Methanol was removed by concentration in vacuo and the resulting aqueous solution was extracted with ethyl acetate three times. The combined organic phase was filtered through silica gel and washed with water and brine, dried (MgSO4) and concentrated. Crystallization from ethyl acetate gave 2-methyl-4-hydroxymethylquinoline (24.6 g, 27%) as a solid. MS(NH3—CI): (M+H)+=174.

출처