Succinic anhydride → 4-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]--4-oxo-butanoic acid

HRID 1195890Notes

Reaction equation

HRID 1195890 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]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1.C([O-])(=O)C.[Na+]>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:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 517045Sodium AcetateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 150273944-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]--4-oxo-butanoic acidYield 44%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

According to the procedure of Example 62, 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine is reacted with 1.0 eq of succinic anhydride in dioxane/water (2:1) in the presence of sodium acetate (2.5 eq). The reaction mixture is diluted with ethyl acetate and is washed with dilute aqueous HCl and then with water. The crude product is purified by recrystallization from methylene chloride. The compound is dissolved in a minimal amount of methanol, diluted with water and lyophylized to give pure 4-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]--4-oxo-butanoic acid (44%); mp 134°-136° C.

Workup

  1. washis washed with dilute aqueous HCl
  2. customThe crude product is purified by recrystallization from methylene chloride
  3. dissolutionThe compound is dissolved in a minimal amount of methanol
  4. additiondiluted with water

Sources & evidence

ORD record
ord-4e56523843eb42f5a13a5db22a098f4a
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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