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Acetyl chloride → N-[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]-N-hydroxy-acetamide

HRID 1461440
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HRID 1461440 반응식
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[C:25]([O-])(=[O:27])[CH3:26].[Na+].C(Cl)(=O)C>O1CCOCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][N:20]([OH:21])[C:25](=[O:27])[CH3:26])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1
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참가 물질

7

반응물 3

HCID 6367Acetyl chloride2회HCID 517045Sodium AcetateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

생성물 1

HCID 15027391N-[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]-N-hydroxy-acetamide수율 47.6%

시약·촉매·용매 3

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매
HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine (1,2 g, 3.5 mmol) and sodium acetate (730 mg, 8.9 mmol) in 120 ml of 1,4-dioxane and 30 ml of water is added dropwise acetyl chloride (420 μl, 5.9 mmol) at 0° C. After 10 minutes additional acetyl chloride (40 ul, 0.6 mmol) is added. The reaction mixture is stirred for 15 minutes, and then is diluted with ethyl acetate. It is washed once with a dilute solution of sodium bicarbonate, once with water, and a saturated solution of sodium chloride The organic phase is further dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is purified by column chromatography on silica gel, eluting first with 1:4 ethyl acetate:methylene chloride then 1:1 ethyl acetate:methylene chloride. Recrystallization from isopropyl ether gives N-[[1-(4-chlorobenzoyl) -5-methoxy-2-methyl-lH-indol-3-yl]methyl]-N-hydroxy-acetamide (645 mg, 47%); mp 160°-161° C.

후처리

  1. washIt is washed once with a dilute solution of sodium bicarbonate, once with water
  2. dry with materiala saturated solution of sodium chloride The organic phase is further dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel
  6. washeluting first with 1:4 ethyl acetate
  7. customRecrystallization from isopropyl ether

출처 및 근거

ORD 기록
ord-2cf63f8a96324200836ac98c4d59f59f
출처 데이터셋
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05075330

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