Lithium Hydroxide → 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxylic acid

HRID 1034467Notes

Reaction equation

HRID 1034467 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])([O:3]CC)=[O:2].[OH-].[Li+]>C(O)C>[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 100382421H-Indole-5-carboxylic acid, 3-[2-(dimethylamino)ethyl]-, ethyl ester

Product 1

HCID 100598183-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[5-Carboethoxy-1H-indol-3-yl]N,N-dimethylethylamine (1.4 g, 5.4 mmol) and lithium hydroxide (0.45 g, 10.8 mmol) in ethanol (40 ml) was heated at 60° C. for 8 hours, then stirred overnight at room temperature. The ethanol was removed in vacuo and the crude residue chromatographed (eluant 20:15:5:1 ether:ethanol:water:ammonia). The acid (0.94 g, 75%) was isolated as a white solid, after precipitation with ether. δ(360 MHz, D6 -DMSO) 2.86 (6H, s), 3.09 (2H, t, J=7 Hz), 3.33 (2H, t, J=7 Hz), 7.22 (1H, s), 7.46 (1H, d, J=9 Hz), 7.78 (1H, dd, J=9 and 2 Hz), 8.12 (1H, s).

Workup

  1. customThe ethanol was removed in vacuo
  2. customthe crude residue chromatographed (eluant 20:15:5:1 ether:ethanol:water:ammonia)

Sources & evidence

ORD record
ord-a4a0bc758f5a480580c736e4bb6bdab2
Source dataset
uspto-grants-1994_05
Patent number
US05317103

Reaction notes

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