Methanol → 2-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetic acid

HRID 589344Notes

Reaction equation

HRID 589344 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[Cl:34])[C:5]([NH:7][C:8]1[CH:30]=[CH:29][C:11]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:22][C:23]([O:25]CC)=[O:24])[C:14]=2[CH3:28])=[CH:10][CH:9]=1)=[O:6].O.[OH-].[Li+].O1CCCC1.CO>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[Cl:34])[C:5]([NH:7][C:8]1[CH:30]=[CH:29][C:11]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:22][C:23]([OH:25])=[O:24])[C:14]=2[CH3:28])=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 90449168ethyl 2-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetate

Product 1

HCID 715717112-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry reaction vessel, ethyl 2-[3-[4-(3,4-dichlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetate (691 mg, 1.39 mmol), lithium hydroxide monohydrate (176 mg, 4.19 mmol), 10 mL tetrahydrofuran, 10 mL methanol, 10 mL water were weighed, and stirred at room temperature for 1 h. The reaction was monitored to be complete by TLC. The solvent was rotate evaporated. It was adjusted to pH=3-4 with 2 N HCl solution. It was filtered, and the filter cake was washed with 20 mL methanol to obtain the product as a white solid 551 mg, at a yield of 84.9%.

Workup

  1. customThe solvent was rotate evaporated
  2. filtrationIt was filtered
  3. washthe filter cake was washed with 20 mL methanol

Sources & evidence

ORD record
ord-7d3f96d2fae543e996be4b297e560562
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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