Lithium hydroxide, monohydrate → 6-Chloro-1-[2-(dimethylamino)ethyl]-1H-indole-3-carboxylic acid

HRID 1716422Notes

Reaction equation

HRID 1716422 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:6]=1)=[O:4].O[Li].O>O.C1COCC1.CO>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]2[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68504879HCID 68504879, compound

Product 1

HCID 685112116-Chloro-1-[2-(dimethylamino)ethyl]-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
40 °C

Procedure

The ester was hydrolyzed in a mixture of H2O/THF/MeOH (ratio 1:1:1) with LiOH.H2O (3 eq.). The reaction mixture was stirred at 40° C. overnight. The acid was extracted several times with EtOAc, and the combined organic phases were dried over Na2SO4. Recrystallisation in Et2O afforded 35 mg (34% overall yield) of the title compound as a white solid.

Workup

  1. extractionThe acid was extracted several times with EtOAc
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customRecrystallisation in Et2O
  4. customafforded

Sources & evidence

ORD record
ord-759ab8b291944e1bb2b19d53d93adfb6
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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