Sodium Hydroxide → HCID 10926215, compound

HRID 1034042Notes

Reaction equation

HRID 1034042 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH:10]=1)=[O:8])([O-:3])=[O:2].[OH-].[Na+]>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:10]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10547793Ethyl 4-[3-(3-nitrobenzoyl)indol-1-yl]butyrate

Product 1

HCID 10926215HCID 10926215, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 4-[3-(3-nitrobenzoyl)indol-1-yl]butyrate (1.60 g), 1N aqueous sodium hydroxide (11 ml) and 1,4-dioxane (50 ml) was stirred at 25° C. for 14 hours. After evaporation of the organic solvent, 1N hydrochloric acid (20 ml) was added to the aqueous solution and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and hexane to give 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid (1.28 g) as-colorless crystals.

Workup

  1. customAfter evaporation of the organic solvent, 1N hydrochloric acid (20 ml)
  2. additionwas added to the aqueous solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-97ce6bb32ce949f9bca50fd9a450e206
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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