Lithium hydroxide, monohydrate → 6-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid

HRID 42422Notes

Reaction equation

HRID 42422 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=2[CH:11]=[C:12]([O:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:13]=1)=[O:4].O[Li].O>C1COCC1.O>[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][O:14][C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[CH:8][N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 674665686-(2-Dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid methyl ester

Product 1

HCID 674640256-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid methyl ester (500 mg, 1.64 mmol) in THF (5 mL) was added LiOH.H2O (200 mg, 4.93 mmol) in water (5 mL). The reaction was heated at reflux for 5 h, at which time the THF was removed under reduced pressure. The remaining mixture was acidified with 1 N HCl (pH ˜6) and extracted with 10% MeOH in chloroform (4×30 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated to yield 6-(2-dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid (400 mg), which was used in the next stage without further purification. LCMS (ES+): m/z=291.30 [M+H].

Workup

  1. temperatureThe reaction was heated
  2. customwas removed under reduced pressure
  3. extractionextracted with 10% MeOH in chloroform (4×30 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-36ac779b270945ba9b39105679cc7a3c
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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