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

HRID 25262

反応式

HRID 25262 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 10149033(2-Methylquinolin-4-yl)methanol収率 27%

試薬・触媒・溶媒 2

HCID 62662Ferrous sulfate heptahydrate触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e61367d030e444008a55ea1f3a232f36
出典データセット
uspto-grants-2005_02
特許番号
US06858626B2

関連ノート

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