Sodium Hydroxide → HCID 10926215, compound

HRID 249136Notes

Reaction equation

HRID 249136 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-9a40cc0b03ce41e3a8d86ed4ac162358
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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