Lithium Hydroxide → Ammonium Hydroxide

HRID 593607Notes

Reaction equation

HRID 593607 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([C:11]2[N:12]([CH3:20])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[N:7][CH:6]=1)C.[Li+].[OH-]>CO>[NH4+:7].[OH-:3].[CH3:20][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[C:9]1[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=1)[C:4]([OH:21])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58215588HCID 58215588, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 58215566HCID 58215566, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(1-methyl-1H-indol-2-yl)-nicotinic acid ethyl ester (Example 102, 0.156 g, 0.55 mmol) and MeOH (5 mL) is added aqueous 1M LiOH (1.4 mL, 1.39 mmol). The reaction is stirred at room temperature for 2.5 h. Purification by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient gives 5-(1-methyl-1H-indol-2-yl)-nicotinic acid. MS (ESI) m/z 253.34 (M+H)+.

Workup

  1. customPurification by reverse phase HPLC with Xbridge Shield RP18 column

Sources & evidence

ORD record
ord-64eeaf3729314669a57590fef086ebea
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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