Sodium Hydroxide → HCID 21938222, compound

HRID 2187753Notes

Reaction equation

HRID 2187753 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-48c3f4ec2f7a413f88f83686dd8fae34
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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