Water → 5-{6-amino-5-[(2,6-dichlorobenzyl)oxy]pyridin-3-yl}-1H-indole-2-carboxylic acid

HRID 425935Notes

Reaction equation

HRID 425935 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([C:17]([O:19]CC)=[O:18])=[CH:11]3)=[CH:4][C:3]=1[O:22][CH2:23][C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31].O.[OH-].[Li+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([C:17]([OH:19])=[O:18])=[CH:11]3)=[CH:4][C:3]=1[O:22][CH2:23][C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 10253528ethyl 5-{6-amino-5-[(2,6-dichlorobenzyl)oxy]pyridin-3-yl}-1H-indole-2-carboxylate

Product 1

HCID 100712225-{6-amino-5-[(2,6-dichlorobenzyl)oxy]pyridin-3-yl}-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of ethyl 5-{6-amino-5-[(2,6-dichlorobenzyl)oxy]pyridin-3-yl}-1H-indole-2-carboxylate (2.5 g, 5.5 mmol) in methanol:water (60 mL:20 mL), lithium hydroxide (0.65 g, 27.1 mmol) was added. The reaction was heated to reflux for overnight. Most of the solvent was evaporated and the mixture was acidified, and stirred for 10 min. The precipitate was filtered out and washed with water to yield 5-{6-amino-5-[(2,6-dichlorobenzyl)oxy]pyridin-3-yl}-1H-indole-2-carboxylic acid as tan solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for overnight
  3. customMost of the solvent was evaporated
  4. filtrationThe precipitate was filtered out
  5. washwashed with water

Sources & evidence

ORD record
ord-d56367e76a7347328b66984ac3bfc43f
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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