Methanol → (2-Methylquinolin-4-yl)methanol

HRID 25262

반응식

HRID 25262 반응식
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH3:24][OH:25]>O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[CH3:3][C:2]1[CH:4]=[C:5]([CH2:24][OH:25])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70602-MethylquinolineHCID 6097028Ammonium Sulfate

생성물 1

HCID 10149033(2-Methylquinolin-4-yl)methanol수율 27%

시약·촉매·용매 2

HCID 62662Ferrous sulfate heptahydrate촉매HCID 962Water용매

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.

후처리

  1. customNitrogen was bubbled into the solution for 20 min
  2. customquenched with 10% sodium hydroxide (pH=9-10)
  3. customMethanol was removed by concentration in vacuo
  4. extractionthe resulting aqueous solution was extracted with ethyl acetate three times
  5. filtrationThe combined organic phase was filtered through silica gel
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customCrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-e61367d030e444008a55ea1f3a232f36
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858626B2

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