Potassium Hydroxide → 6-Chloro-5-(4-ethoxyphenyl)-1H-indole-3-carboxylic acid

HRID 338304Notes

Reaction equation

HRID 338304 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:23])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4].[OH-:26].[K+]>COCCOC>[Cl:23][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:26])=[O:4])=[CH:6][NH:7]2)=[CH:12][C:11]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH3:22])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866986512,2,2-trichloro-1-(6-chloro-5-(4-ethoxyphenyl)-1H-indol-3-yl)ethanone

Product 1

HCID 866986506-Chloro-5-(4-ethoxyphenyl)-1H-indole-3-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2,2,2-trichloro-1-(6-chloro-5-(4-ethoxyphenyl)-1H-indol-3-yl)ethanone (70.0 mg, 0.17 mmol) in DME (1 mL) was added 1N KOH (0.71 mmol, 0.71 mL). The reaction mixture was stirred at room temperature for 12 hours, and concentrated in vacuo. The crude material was diluted with water (5 mL), and acidified to pH 2.5 with 1N HCl to form a white precipitate. The precipitate was filtered, washed with water (20 mL) and dried under vacuum to provide the title compound (37 mg, 70%) as an off-white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude material was diluted with water (5 mL)
  3. customto form a white precipitate
  4. filtrationThe precipitate was filtered
  5. washwashed with water (20 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-244b849b38114008911dcfe7b3109046
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

Loading…