Water → (8-Methoxyquinolin-5-yl)methanol

HRID 2374166노트

반응식

HRID 2374166 반응식
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](O)=[N:8]2.[C:14](=O)([O-])[O-:15].[K+].[K+].CI.O>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:15][CH3:14])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178519443HCID 178519443, 화합물

생성물 1

HCID 7172171(8-Methoxyquinolin-5-yl)methanol수율 90.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-(Hydroxymethyl) quinolinol (6.7 g, 38 mmol) was dissolved in DMF (38 mL) and treated with potassium carbonate (16 g, 116 mmol) followed by methyl iodide (2.9 mL, 6.8 g, 48 mmol). The mixture was allowed to stir overnight at RT, then poured into a separatory funnel with water and extracted 3× DCM. The organic layer was dried over Na2SO4, and concentrated to give solid 5-hydroxymethyl-8-methoxyquinoline (6.5 g). 1H NMR (CDCl3) δ 8.97 (d, 1H), 8.51 (d, 1H) 7.49 (m, 2H), 6.99 (d, 1H), 5.05 (s, 2H), 4.09 (s, 3H).

후처리

  1. extractionextracted 3× DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2172f9bda830476993ec08712e0f5d53
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462600B2

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