Methanol → HCID 19024838, compound

HRID 249157Notes

Reaction equation

HRID 249157 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[CH:6]=[C:5]2[C:19](=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.[OH-].[Na+].CO>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[C:5]2[C:19](=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19024719HCID 19024719, compound

Product 1

HCID 19024838HCID 19024838, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 4-[5-chloro-3-(3-nitrobenzoyl)indol-1-yl]butyrate (2.00 g), 1N aqueous sodium hydroxide (7.5 ml), methanol (35 ml) and 1,4-dioxane (35 ml) was stirred at 25° C. for 6 hours. After evaporation of the organic solvent, 1N hydrochloric acid (15 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 washed with hot ethanol to give 4-[5-chloro-3-(3-nitrobenzoyl)indol-1-yl]butyric acid (1.77 g) as colorless crystals.

Workup

  1. customAfter evaporation of the organic solvent, 1N hydrochloric acid (15 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. washThe crystalline residue was washed with hot ethanol

Sources & evidence

ORD record
ord-9694561daa1a484ca613e2e5027c8101
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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