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

HRID 1167349

反応式

HRID 1167349 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5ecd000c1aea4027944e5d4c242af64e
出典データセット
uspto-grants-2003_09
特許番号
US06617346B1

関連ノート

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