Sodium Hydroxide → N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid

HRID 1582628Notes

Reaction equation

HRID 1582628 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([O:20]CC)=[O:19]>C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11233838Ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate

Product 1

HCID 9949615N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (2M, 3 ml) was added to a stirred solution of ethyl N-(3,4-dichlorobenzyl)-5-hydroxyindole-2-carboxylate (0.1 g) in THF (3 ml) and methanol (1.5 ml). The reaction was stirred at ambient temperature for 4 hours. The reaction was concentrated in vacuo and the residue was dissolved in water (5 ml). The solution was acidified by the addition of aqueous hydrochloric acid (2M, 4 ml) precipitating the product as a white solid. The product was filtered, washed with water and dried in vacuo to yield the title compound (82 mg, 89%). NMR: δ 5.77 (s, 2H), 6.81 (dd, 1H), 6.89 (dd, 1H), 6.95 (d, 1H), 7.13 (s, 1H), 7.26 (d, 1H), 7.34 (d, 1H), 7.52 (d, 1H), 9.01 (s, 1H), 12.85 (s, 1H); m/z 334 (M−H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (5 ml)
  3. additionThe solution was acidified by the addition of aqueous hydrochloric acid (2M, 4 ml)
  4. customprecipitating the product as a white solid
  5. filtrationThe product was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d02d41d7a6334f1490690e1b691924d9
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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