Sodium Hydroxide → HCID 21938222, compound

HRID 1242143Notes

Reaction equation

HRID 1242143 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[CH:13]=2)[NH:8][C:7]=1[CH3:19])=[O:5].[OH-].[Na+]>C(O)C>[C:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:19])=[C:6]2[C:4](=[O:5])[C:3]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:2]=1[Cl:1])([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21938259HCID 21938259, compound

Product 1

HCID 21938222HCID 21938222, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2,4-Dichlorobenzoyl)-5-(methoxycarbonyl)-2-methylindole (0.60 g) is suspended in ethanol (10 ml), to which is added an aqueous solution of 1.5 M sodium hydroxide (5 ml), and heated under reflux for 3 hours. The reaction mixture is concentrated under reduced pressure, and the residue is made acidic with water and 3 M HCl added thereto. The crystal formed is taken out through filtration, then suspended in ethanol-toluene, and concentrated under reduced pressure for azeotropic dehydration. Next, this is dried on calcium chloride in a vacuum desiccator to obtain a crystal of 5-carboxy-3-(2,4-dichlorobenzoyl)-2-methylindole (76) (0.56 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionadded
  5. customThe crystal formed
  6. filtrationis taken out through filtration
  7. concentrationconcentrated under reduced pressure for azeotropic dehydration
  8. customNext, this is dried on calcium chloride in a vacuum desiccator

Sources & evidence

ORD record
ord-3f72fb1086da48b298840a724e40df74
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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