Sodium Hydroxide → 3-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acid

HRID 1108715Notes

Reaction equation

HRID 1108715 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]C)=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:5]=1[CH2:25][CH2:26][CH3:27])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:5]=1[CH2:25][CH2:26][CH3:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10200004Methyl 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylate

Product 1

HCID 98206883-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylate (125 mg) in ethanol (6 ml) was added 1N aqueous sodium hydroxide (0.7 ml), and the mixture was stirred under reflux for 1 hour. The resulting mixture was evaporated in vacuo, and the residue was acidified with 1N hydrochloric acid (0.75 ml) and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with isopropyl ether to give 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acid (78 mg) as solid.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe resulting mixture was evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-3639c7ed38834f1da789e208e41704d8
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

Loading…