Acetic Anhydride → 2-[2-(4-Acetamido-phenyl)-1-propyl-1H-indole-6-yloxy]-2-methyl-propanoic acid ethylester

HRID 66898Notes

Reaction equation

HRID 66898 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([CH3:29])([O:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[N:14]2[CH2:17][CH2:18][CH3:19])=[CH:10][CH:9]=1)[CH3:6])[CH3:2].[H][H].[C:33](OC(=O)C)(=[O:35])[CH3:34]>[Ni]>[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:33](=[O:35])[CH3:34])=[CH:22][CH:21]=3)[N:14]2[CH2:17][CH2:18][CH3:19])=[CH:10][CH:9]=1)([CH3:29])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 536627632-Methyl-2-[2-(4-nitro-phenyl)-1-propyl-1H-indole-6-yloxy]-propanoic acid ethylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 211536462-[2-(4-Acetamido-phenyl)-1-propyl-1H-indole-6-yloxy]-2-methyl-propanoic acid ethylester

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

An amount of 5.4 g (13 m mole) of 2-methyl-2-[2-(4-nitro-phenyl)-1-propyl-1H-indole-6-yloxy]-propanoic acid ethylester and 2.5 g of Raney-Nickel were suspended in 150 ml of acetic anhydride and hydrogenated at a pressure of 5 bar with hydrogen at 20° C. Subsequently the catalyst was filtered off and the filtrate was evaporated. The resulting residue was chromatographed on silicagel (solvent: toluene/acetone (3:1)), the eluates were evaporated, and the residue was triturated with petroleum ether/ether and suction filtered.

Workup

  1. filtrationSubsequently the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe resulting residue was chromatographed on silicagel (solvent: toluene/acetone (3:1))
  4. customthe eluates were evaporated
  5. customthe residue was triturated with petroleum ether/ether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-adb0aaa288864ce29ff1b215eac15483
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

Loading…