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

HRID 1195887
Notes
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Reaction equation

HRID 1195887 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6367Acetyl chloride2×HCID 517045Sodium AcetateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

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

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-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 μl, 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-1H-indol-3-yl]methyl]-N-hydroxy-acetamide (645 mg, 47%); mp 160°-161° C.

Workup

  1. washIt is washed once with a dilute solution of sodium bicarbonate, once with water
  2. dry with materialThe 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

Sources & evidence

ORD record
ord-ee9493e7e02846e0b27e4f1ef0a7a086
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05112846

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes