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

HRID 1054648Notes

Reaction equation

HRID 1054648 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 1 N 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 1 N 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-a8a8799fcbd141cb828bcccc302835e2
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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