Lithium Hydroxide → 4-m-tolyloxy-1H-indole-2-carboxylic acid

HRID 1929160Notes

Reaction equation

HRID 1929160 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.[Li+].[OH-]>CO.O>[C:18]1([CH3:22])[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 668417024-m-Tolyloxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668416084-m-tolyloxy-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

136 (520 mg, 1.761 mmol) is dissolved in 10 ml of methanol and treated with a solution of LiOH (84.3 mg, 3.52 mmol) in 5 ml of water. The mixture is stirred at room temperature for 18 hours. After evaporation, the crude product is acidified at 0° C. with 2M HCl and extracted with ethyl acetate. The organic layers are dried over sodium sulphate and evaporated.

Workup

  1. customAfter evaporation
  2. customis acidified at 0° C. with 2M HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layers are dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-34b3614450c14a8c943aa10640958b3f
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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