Methyl iodide → Benzamide, 2-hydroxy-6-methoxy-

HRID 1167349

반응식

HRID 1167349 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH2:6])=[O:5].[C:12](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5]

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 766022,6-Dihydroxybenzamide

생성물 1

HCID 173610Benzamide, 2-hydroxy-6-methoxy-수율 69.6%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2,6-dihydroxybenzamide (2 g, 12.66 mmol) in dimethylformamide (100 mL) were added cesium carbonate (3.922 g, 12.03 mmol) and methyl iodide (756 μL, 12.03 mmol). The reaction mixture was stirred at room temperature for 36 h and was taken in 200 mL of ethyl acetate and diethyl ether (1:1 ratio). It was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 25% ethyl acetate in hexanes yielded 2-hydroxy-6-methoxy-benzamide (1.4 g, 66%).

후처리

  1. washIt was washed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solid was then filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  6. washeluting with 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-5ecd000c1aea4027944e5d4c242af64e
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617346B1

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